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Journal articles on the topic 'The asymmetric Mannich reaction'

Author: Grafiati

Published: 24 April 2022

Last updated: 30 July 2025

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1

Singh, Girija S. "Greener Approaches to Selected Asymmetric Addition Reactions Relevant to Drug Development." Current Organic Chemistry 25, no. 13 (2021): 1497–522. http://dx.doi.org/10.2174/1385272825666210519100457.

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Asymmetric organic synthesis is of paramount importance in the development of drugs. Asymmetric addition reactions such as aldol reaction, Michael addition, and Mannich addition reactions are important carbon-carbon bond-forming reactions and have been employed in the synthesis of a broad range of biologically important molecules. Many of these reactions have been developed under solvent-free conditions or in greener solvents like water. Several reactions have been developed at room temperature or by using a non-conventional energy source such as microwave irradiation. Several greener catalyst

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2

Sodeoka, Mikiko, and Yoshitaka Hamashima. "Synthesis of optically active heterocyclic compounds using Pd-catalyzed asymmetric reactions as a key step." Pure and Applied Chemistry 80, no. 4 (2008): 763–76. http://dx.doi.org/10.1351/pac200880040763.

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Highly enantioselective Pd(II)-catalyzed Michael addition, Mannich-type reaction, aldol reaction, fluorination, conjugate addition of amine, and conjugate reduction have been developed. Asymmetric synthesis of biologically interesting heterocyclic compounds, calycotomine, BMS-204352, torcetrapib, and warfarin, was achieved by using these Pd-catalyzed asymmetric reactions as a key step.

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3

Lee, Hyo-Jun, Natarajan Arumugam, Abdulrahman Almansour, Raju Kumar, and Keiji Maruoka. "Design of New Amino Tf-Amide Organocatalysts: Environmentally Benign Approach to Asymmetric Aldol Synthesis." Synlett 30, no. 04 (2018): 401–4. http://dx.doi.org/10.1055/s-0037-1610408.

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A new type of optically pure primary amino aromatic Tf-amide organocatalyst can be easily prepared from 8-amino-1-tetralone, and its chemical behavior was investigated in the context of asymmetric aldol and Mannich reactions. Most notably, the asymmetric aldol reaction proceeded smoothly in brine.

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4

Bagheri, Ilnaz, Leila Mohammadi, Vahideh Zadsirjan, and Majid M. Heravi. "Organocatalyzed Asymmetric Mannich Reaction: An Update." ChemistrySelect 6, no. 5 (2021): 1008–66. http://dx.doi.org/10.1002/slct.202003034.

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5

Córdova, Armando. "The Direct Catalytic Asymmetric Mannich Reaction." Accounts of Chemical Research 37, no. 2 (2004): 102–12. http://dx.doi.org/10.1021/ar030231l.

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6

Dudek, Agata, and Jacek Mlynarski. "Iron-Catalyzed Asymmetric Nitro-Mannich Reaction." Journal of Organic Chemistry 82, no. 20 (2017): 11218–24. http://dx.doi.org/10.1021/acs.joc.7b01786.

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7

Chen, Jianfeng, Xing Gong, Jianyu Li, et al. "Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction." Science 360, no. 6396 (2018): 1438–42. http://dx.doi.org/10.1126/science.aat4210.

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Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N-diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the subst

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8

Nomura, Miku, Zubeda Begum, Chigusa Seki та ін. "Thiourea fused γ-amino alcohol organocatalysts for asymmetric Mannich reaction of β-keto active methylene compounds with imines". RSC Advances 13, № 6 (2023): 3715–22. http://dx.doi.org/10.1039/d2ra08317e.

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Catalytic functionality of new optically active thiourea fused γ-amino alcohols was examined in the asymmetric Mannich reaction of β-keto active methylene compounds with imines to afford chiral Mannich products, β-amino keto compounds..

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9

Rachwalski, Michał, Aleksandra Buchcic-Szychowska, and Stanisław Leśniak. "Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update." Symmetry 13, no. 10 (2021): 1762. http://dx.doi.org/10.3390/sym13101762.

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The main purpose of this review article is to present selected asymmetric synthesis reactions in which chemical and stereochemical outcomes are dependent on the use of an appropriate chiral catalyst. Optically pure or enantiomerically enriched products of such transformations may find further applications in various fields. Among an extremely wide variety of asymmetric reactions catalyzed by chiral systems, we are interested in: asymmetric cyclopropanation, Friedel–Crafts reaction, Mannich and Michael reaction, and other stereoselective processes conducted in the presence of zinc ions. This pa

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10

Yoshida, Yasushi, Maho Aono, Takashi Mino та Masami Sakamoto. "Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt". Beilstein Journal of Organic Chemistry 21 (12 березня 2025): 547–55. https://doi.org/10.3762/bjoc.21.43.

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β-Amino cyanoesters are important scaffolds because they can be transformed into useful chiral amines, amino acids, and amino alcohols. Halogen bonding, which can be formed between halogen atoms and electron-rich chemical species, is attractive because of its unique interaction in organic synthesis. Chiral halonium salts have been found to have strong halogen-bonding-donor abilities and work as powerful asymmetric catalysts. Recently, we have developed binaphthyl-based chiral halonium salts and applied them in several enantioselective reactions, which formed the corresponding products in high

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11

Zhang, Suoqin, Guangliang Zhang, Tianyun Zhou, et al. "Chiral VAPOL Imidodiphosphoric Acid-Catalyzed Asymmetric Vinylogous Mannich Reaction for the Synthesis of Butenolides." Synlett 29, no. 15 (2018): 2006–10. http://dx.doi.org/10.1055/s-0037-1610232.

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Chiral butenolides were synthesized by the enantioselective vinylogous Mannich reaction. Chiral (VAPOL)-type imidodiphosphoric acids are efficient catalysts for the asymmetric vinylogous Mannich (AVM) reaction of aldimines and trimethylsiloxyfuran in toluene. Under the optimized conditions, a series of butenolides were obtained with high yields (up to 98%) and enantioselectivities (up to 97% ee) as well as excellent diastereoselectivities (up to 99:1 dr).

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12

Xiao-Hua, Cai, Guo Hui, and Xie Bing. "Recent progress in the asymmetric Mannich reaction." European Journal of Chemistry 3, no. 2 (2012): 258–66. http://dx.doi.org/10.5155/eurjchem.3.2.258-266.536.

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13

Liu, Li-Juan, and Jin-Tao Liu. "2-Chlorotetrafluoroethanesulfinamide induced asymmetric vinylogous Mannich reaction." Tetrahedron 70, no. 6 (2014): 1236–45. http://dx.doi.org/10.1016/j.tet.2013.12.071.

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14

Wu, Ling-Ling, Yang Xiang, Da-Cheng Yang, Zhi Guan, and Yan-Hong He. "Biocatalytic asymmetric Mannich reaction of ketimines using wheat germ lipase." Catalysis Science & Technology 6, no. 11 (2016): 3963–70. http://dx.doi.org/10.1039/c5cy01923k.

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15

Buchcic, Aleksandra, Anna Zawisza, Stanisław Leśniak, Justyna Adamczyk, Adam Marek Pieczonka, and Michał Rachwalski. "Enantioselective Mannich Reaction Promoted by Chiral Phosphinoyl-Aziridines." Catalysts 9, no. 10 (2019): 837. http://dx.doi.org/10.3390/catal9100837.

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In this study, a set of enantiomerically pure aziridines bearing a phosphine oxide moiety were prepared in high yields and tested as chiral catalysts in the direct asymmetric Mannich reaction of hydroxyacetone, an amine (p-anisidine), and various aromatic aldehydes. The appropriate Mannich adducts were formed in chemical yields from moderate to good with a high level of enantio- and diastereoselectivity. The best results were obtained using the catalysts bearing a free NH-aziridine subunit.

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16

Li, Ziyi, Hua Gao, Haibo Mei, Guangwei Wu, Vadim A. Soloshonok, and Jianlin Han. "Synthesis of Aminoalkyl Sclareolide Derivatives and Antifungal Activity Studies." Molecules 28, no. 10 (2023): 4067. http://dx.doi.org/10.3390/molecules28104067.

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Sclareolide was developed as an efficient C-nucleophilic reagent for an asymmetric Mannich addition reaction with a series of N-tert-butylsulfinyl aldimines. The Mannich reaction was carried out under mild conditions, affording the corresponding aminoalkyl sclareolide derivatives with up to 98% yield and 98:2:0:0 diastereoselectivity. Furthermore, the reaction could be performed on a gram scale without any reduction in yield and diastereoselectivity. Additionally, deprotection of the obtained Mannich addition products to give the target sclareolide derivatives bearing a free N-H group was demo

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17

Unhale, Rajshekhar A., Milon M. Sadhu, Sumit K. Ray, Rayhan G. Biswas та Vinod K. Singh. "A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines". Chemical Communications 54, № 28 (2018): 3516–19. http://dx.doi.org/10.1039/c8cc01436a.

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A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-aryl-3-hydroxyisoindolinones has been demonstrated. The reaction proceeds smoothly under mild reaction conditions.

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18

Cai, Hao, Yu Zhou, Dong Zhang, Jinyi Xu, and Hong Liu. "A Mannich/cyclization cascade process for the asymmetric synthesis of spirocyclic thioimidazolidineoxindoles." Chem. Commun. 50, no. 94 (2014): 14771–74. http://dx.doi.org/10.1039/c4cc06000h.

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19

Zhang, Shixiong, Ping Deng, Jing Zhou, et al. "A novel homobimetallic nickel complex for the asymmetric direct Mannich reaction of imines: a practical method on a multi-gram scale." Chemical Communications 53, no. 96 (2017): 12914–17. http://dx.doi.org/10.1039/c7cc06468c.

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20

Luo, Yuan, Ke-Xin Xie, Deng-Feng Yue, Xiao-Mei Zhang, Xiao-Ying Xu, and Wei-Cheng Yuan. "An organocatalytic asymmetric Mannich reaction of pyrazoleamides with cyclic trifluoromethyl ketimines: enantioselective access to dihydroquinazolinone skeletons." Organic & Biomolecular Chemistry 16, no. 18 (2018): 3372–75. http://dx.doi.org/10.1039/c8ob00707a.

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21

Verkade, Jorge M. M., Lieke J. C. van Hemert, Peter J. L. M. Quaedflieg, and Floris P. J. T. Rutjes. "Organocatalysed asymmetric Mannich reactions." Chem. Soc. Rev. 37, no. 1 (2008): 29–41. http://dx.doi.org/10.1039/b713885g.

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22

Marques, Carolina, and Pedro Brandão. "The Asymmetric Petasis Borono-Mannich Reaction: Insights on the Last 15 Years." Catalysts 13, no. 6 (2023): 1022. http://dx.doi.org/10.3390/catal13061022.

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The Petasis borono-Mannich reaction, commonly described as the Petasis reaction, was one of the latest famous multicomponent reactions described in the literature. Currently celebrating its 30th anniversary since it was first reported by Petasis and Akritopoulou in 1993, this reaction has emerged as a powerful tool for the synthesis of biologically relevant molecules (such as substituted amines or amino acids), among others. This three-component catalyst-free reaction (the classic model), involving the coupling of an aldehyde, an amine, and a boronic acid, enables the synthesis of polysubstitu

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23

Zhang, Yan-Ping, Yong You, Jun-Qing Yin, Zhen-Hua Wang, Jian-Qiang Zhao, and Wei-Cheng Yuan. "Progress in Catalytic Asymmetric Reactions with 7-Azaindoline as the Directing Group." Molecules 28, no. 23 (2023): 7898. http://dx.doi.org/10.3390/molecules28237898.

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α-Substituted-7-azaindoline amides and α,β-unsaturated 7-azaindoline amides have emerged as new versatile synthons for various metal-catalyzed and organic-catalyzed asymmetric reactions, which have attracted much attention from chemists. In this review, the progress of research on 7-azaindoline amides in the asymmetric aldol reaction, the Mannich reaction, the conjugate addition, the 1,3-dipole cycloaddition, the Michael/aldol cascade reaction, aminomethylation and the Michael addition-initiated ring-closure reaction is discussed. The α-substituted-7-azaindoline amides, as nucleophiles, are cl

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24

Rao, Kadiyala Srinivasa, Pambala Ramesh, L. Raju Chowhan, and Rajiv Trivedi. "Asymmetric Mannich reaction: highly enantioselective synthesis of 3-amino-oxindoles via chiral squaramide based H-bond donor catalysis." RSC Advances 6, no. 87 (2016): 84242–47. http://dx.doi.org/10.1039/c6ra16877a.

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A facile formation of 3-aminooxindole derivatives from the reaction of 1,3-diketones with isatin (N-Boc) via an asymmetric Mannich reaction catalyzed by chiral cinchona alkaloid based squaramide containing H-bond donor catalysts.

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25

Mukhopadhyay, Soumendranath, and Subhas Chandra Pan. "An organocatalytic asymmetric Mannich reaction for the synthesis of 3,3-disubstituted-3,4-dihydro-2-quinolones." Organic & Biomolecular Chemistry 16, no. 30 (2018): 5407–11. http://dx.doi.org/10.1039/c8ob01399c.

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26

Yu, Jin-Sheng, Hidetoshi Noda, Naoya Kumagai та Masakatsu Shibasaki. "Direct Catalytic Asymmetric Mannich-Type Reaction of an α-CF3 Amide to Isatin Imines". Synlett 30, № 04 (2018): 488–92. http://dx.doi.org/10.1055/s-0037-1611642.

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An α-CF3 amide underwent direct asymmetric Mannich-type reaction to isatin imines in the presence of a chiral catalyst comprising a soft Lewis acid Cu(I), a chiral bisphosphine ligand, and Barton’s base. The Mannich adduct was converted in one step into a unique tricycle bearing a trifluoromethylated chiral center and an α-tertiary amine moiety.

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27

Xie, Chen, Wanxing Sha, Yi Zhu, Jianlin Han, Vadim A. Soloshonok та Yi Pan. "Asymmetric synthesis of C–F quaternary α-fluoro-β-amino-indolin-2-ones via Mannich addition reactions; facets of reactivity, structural generality and stereochemical outcome". RSC Advances 7, № 10 (2017): 5679–83. http://dx.doi.org/10.1039/c6ra27710a.

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An asymmetric detrifluoroacetylative Mannich reaction between in situ generated tertiary enolates and sulfinyl-imines has been explored. The reaction provides a new access to α-fluoro-β-amino-indolin-2-ones with tetrasubstituted fluorinated stereogenic center.

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28

Wu, Wei, Yan Wang, Jing Guo та ін. "Asymmetric acyl-Mannich reaction of isoquinolines with α-(diazomethyl)phosphonate and diazoacetate catalyzed by chiral Brønsted acids". Chemical Communications 56, № 76 (2020): 11235–38. http://dx.doi.org/10.1039/d0cc03201h.

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29

Shu, Siwei, Zhao Liu, Yukui Li, Zhuofeng Ke, and Yan Liu. "Diastereoselectivity in a cyclic secondary amine catalyzed asymmetric Mannich reaction: a model rationalization from DFT studies." Organic Chemistry Frontiers 5, no. 14 (2018): 2148–57. http://dx.doi.org/10.1039/c8qo00424b.

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30

Wu, Lei, Guangxun Li, Migu He, Yingwei Wang, Gang Zhao, and Zhuo Tang. "First example of an organocatalytic asymmetric Mannich reaction between aldimines of glycinates and sulphonyl imines." Canadian Journal of Chemistry 94, no. 9 (2016): 769–72. http://dx.doi.org/10.1139/cjc-2016-0089.

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The catalytic enantioselective Mannich-type reaction between glycinate Schiff base and imines has been one of the most efficient routes for accessing α,β-diamino acids. However, the glycinate Schiff bases used in the references were almost ketimines. Only several examples of aldimines were used in the presence of metal catalyst. We developed the first example of an asymmetric direct Mannich reaction using aldimines of glycinates instead of ketimines of glycinates. The reaction was well catalyzed by chiral guanidine with high yield (up to 92%) and moderate stereoselectivity (up to 65%).

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31

Zhao, Mei-Xin, Lei Jing, Hao Zhou, and Min Shi. "Cinchona alkaloid thiourea mediated asymmetric Mannich reaction of isocyanoacetates with isatin-derived ketimines and subsequent cyclization: enantioselective synthesis of spirooxindole imidazolines." RSC Advances 5, no. 92 (2015): 75648–52. http://dx.doi.org/10.1039/c5ra17075c.

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The organocatalyzed asymmetric Mannich reaction of isocyanoacetates with isatin ketimines and subsequent cyclization were developed, leading to spirooxindole imidazolines in high yields and excellent stereoselectivities.

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32

Yang, Zinan, Huakang He, Rui Tian, et al. "A zinc/PyBisulidine catalyzed asymmetric Mannich reaction of N-tosyl imines with 3-acyloxy-2-oxindoles." Organic & Biomolecular Chemistry 19, no. 34 (2021): 7460–69. http://dx.doi.org/10.1039/d1ob01328a.

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33

Li, Jin-Shan, Yong-Jie Liu, Shen Li, and Jun-An Ma. "Chiral phosphoric acid-catalyzed direct asymmetric mannich reaction of cyclicC-acylimines with simple ketones: facile access to C2-quaternary indolin-3-ones." Chemical Communications 54, no. 66 (2018): 9151–54. http://dx.doi.org/10.1039/c8cc05125a.

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34

Zhu, Jing-Yan, Wu-Lin Yang, Yang-Zi Liu, Shao-Jing Shang, and Wei-Ping Deng. "A copper(i)-catalyzed asymmetric Mannich reaction of glycine Schiff bases with isatin-derived ketimines: enantioselective synthesis of 3-substituted 3-aminooxindoles." Organic Chemistry Frontiers 5, no. 1 (2018): 70–74. http://dx.doi.org/10.1039/c7qo00691h.

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35

Fujii, Akio, Emiko Hagiwara, and Mikiko Sodeoka. "Asymmetric Mannich-Type Reaction Catalyzed by Palladium Complexes." Journal of Synthetic Organic Chemistry, Japan 58, no. 8 (2000): 728–35. http://dx.doi.org/10.5059/yukigoseikyokaishi.58.728.

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36

Guo, Qi-Xiang, Hua Liu, Chang Guo, Shi-Wei Luo, Yi Gu, and Liu-Zhu Gong. "Chiral Brønsted Acid-Catalyzed Direct Asymmetric Mannich Reaction." Journal of the American Chemical Society 129, no. 13 (2007): 3790–91. http://dx.doi.org/10.1021/ja068236b.

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37

List, Benjamin. "The Direct Catalytic Asymmetric Three-Component Mannich Reaction." Journal of the American Chemical Society 122, no. 38 (2000): 9336–37. http://dx.doi.org/10.1021/ja001923x.

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38

Deng, L., J. Song, and Y. Wang. "Organocatalytic Asymmetric Mannich Reaction of Malonates with Imines." Synfacts 2006, no. 6 (2006): 0612. http://dx.doi.org/10.1055/s-2006-941781.

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39

Krištofíková, Dominika, Mária Mečiarová, Erik Rakovský, and Radovan Šebesta. "Mechanochemically Activated Asymmetric Organocatalytic Domino Mannich Reaction-Fluorination." ACS Sustainable Chemistry & Engineering 8, no. 38 (2020): 14417–24. http://dx.doi.org/10.1021/acssuschemeng.0c04260.

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40

Arteaga, Fernando Arteaga, Zijian Liu, Lennart Brewitz, et al. "Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides." Organic Letters 18, no. 10 (2016): 2391–94. http://dx.doi.org/10.1021/acs.orglett.6b00879.

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41

Rodríguez, Belén, and Carsten Bolm. "Thermal Effects in the Organocatalytic Asymmetric Mannich Reaction." Journal of Organic Chemistry 71, no. 7 (2006): 2888–91. http://dx.doi.org/10.1021/jo060064d.

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42

Suzuki, Yuta, Ryo Yazaki, Naoya Kumagai, and Masakatsu Shibasaki. "Direct Catalytic Asymmetric Mannich-Type Reaction of Thioamides." Angewandte Chemie International Edition 48, no. 27 (2009): 5026–29. http://dx.doi.org/10.1002/anie.200901588.

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43

Suzuki, Yuta, Ryo Yazaki, Naoya Kumagai, and Masakatsu Shibasaki. "Direct Catalytic Asymmetric Mannich-Type Reaction of Thioamides." Angewandte Chemie 121, no. 27 (2009): 5126–29. http://dx.doi.org/10.1002/ange.200901588.

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44

Li, Gonglin, Yan Zhang, Hongkun Zeng, Xiaoming Feng, Zhishan Su, and Lili Lin. "Water enables diastereodivergency in bispidine-based chiral amine-catalyzed asymmetric Mannich reaction of cyclic N-sulfonyl ketimines with ketones." Chemical Science 13, no. 15 (2022): 4313–20. http://dx.doi.org/10.1039/d2sc00446a.

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A diastereodivergent asymmetric Mannich reaction of cyclic N-sulfonyl ketimines with ketones is realized by employing bispidine-based chiral amine as catalyst and additional water switching the diastereoselectivity.

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45

Zhang, Qing-Da, Bo-Liang Zhao, Bing-Yu Li, and Da-Ming Du. "Squaramide-catalyzed asymmetric Mannich reactions between 3-fluorooxindoles and pyrazolinone ketimines." Organic & Biomolecular Chemistry 17, no. 30 (2019): 7182–91. http://dx.doi.org/10.1039/c9ob01350d.

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Squaramide-catalyzed asymmetric Mannich reaction between 3-fluorooxindoles and pyrazolinone ketimines afforded fluorinated amino-pyrazolone-oxindoles with two quaternary stereocenters in good to excellent yields with excellent stereoselectivities.

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46

Kolodiazhna, Anastasy O., та Oleg I. Kolodiazhnyi. "Сatalytic Asymmetric Synthesis of C-Chiral Phosphonates". Symmetry 14, № 9 (2022): 1758. http://dx.doi.org/10.3390/sym14091758.

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The current review is devoted to the achievements in the development of methods for the catalytic asymmetric synthesis of phosphonates containing a chiral center in the side chain. C-chiral phosphonates are widely represented among natural compounds with various biological activities as insecticides, herbicides, antibiotics, and bioregulators. Synthetic representatives of this class have found practical application as biologically active compounds. The review summarizes methods of asymmetric metal complex catalysis and organocatalysis as applied to such reactions as phospha-aldol reaction, two

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47

Mei, Haibo, Yiwen Xiong, Chen Xie, Vadim A. Soloshonok, Jianlin Han, and Yi Pan. "Concise and scalable asymmetric synthesis of 5-(1-amino-2,2,2-trifluoroethyl)thiazolo[3,2-b][1,2,4]triazoles." Org. Biomol. Chem. 12, no. 13 (2014): 2108–13. http://dx.doi.org/10.1039/c3ob42348d.

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48

Capobianco, Amedeo, Antonia Di Mola, Valentina Intintoli, et al. "Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study." RSC Advances 6, no. 38 (2016): 31861–70. http://dx.doi.org/10.1039/c6ra05488a.

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The first asymmetric synthesis of 3-amino-substituted isoindolinones was accomplished via cascade hemiaminal-heterocyclization-intramolecular aza-Mannich reaction of amines and 2-formylbenzonitriles using chiral phase transfer conditions (PTC).

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49

Zheng, Yao, and Da-Ming Du. "Asymmetric Mannich/Cyclization Reaction of 2-Benzothiazolimines and 2-Isothiocyano-1-indanones to Construct Chiral Spirocyclic Compounds." Molecules 29, no. 13 (2024): 2958. http://dx.doi.org/10.3390/molecules29132958.

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An efficient and practical organocatalyzed asymmetric Mannich/cyclization tandem reaction strategy of 2-benzothiazolimines and 2-isothiocyanato-1-indanones was developed, and novel spirocyclic compounds containing benzothiazolimine and indanone scaffolds were obtained. This chiral thiourea-catalyzed Mannich/cyclization tandem reaction offers chiral spirocyclic compounds with continuous tertiary and quaternary stereocenters in good to high yields (up to 90%) with excellent diastereoselectivities (up to >20:1 dr) and enantioselectivities (up to 98% ee) at −18 °C. Additionally, the scaled-up s

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50

Seebach, Dieter, Martin Schiess, and W. Bernd Schweizer. "On the Stereochemical Course of Asymmetric Mannich Reactions." CHIMIA 39, no. 9 (1985): 272. https://doi.org/10.2533/chimia.1985.272.

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Abstract:

In the TiCl4-mediated Mannich reaction, β-amino ketones are obtained with diastereoselectivities of 70-95%. The configuration of the major isomer obtained from benzaldehyde, piperidine, and cyclohexanone [2-(α-piperidinobenzyl)cyclohexanone 1] is shown by X-ray crystallography to be unlike (u, cf. Fig. 1). Thus, the trigonal centers combine to form the C–C bond with relative topicity like (lk, 3). Possible mechanisms of the reaction are briefly discussed.

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