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Journal articles on the topic 'Stereogenic quaternary center'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Chen, Hui, Cui Wang, Dongwa Wen, Yabo Deng, Xin Liu, Xueting Liu, Jiang Zhang, and Wenjin Yan. "The Catalytic Asymmetric Construction of Trifluoromethylated Quaternary Carbon-Containing Thiochromans." Synthesis 51, no. 17 (May 15, 2019): 3327–35. http://dx.doi.org/10.1055/s-0037-1611547.

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Trifluoromethylated chiral quaternary stereogenic carbon center at 2-position of thiochromans has been constructed through organocatalyzed Michael-aldol reaction. With quinine squaramide as catalyst, the reaction of 2-mercaptobenzaldehyde with β-aryl-β-CF3 enones or β-alkyl-β-CF3 enones gave 2-CF3-thiochromans bearing three contiguous stereogenic centers in good to excellent diastereoselectivities, enantioselectivities, and yields.

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2

Rafiński, Zbigniew. "NHC-Catalyzed Organocatalytic Asymmetric Approach to 2,2-Disubstituted Benzofuran-3(2H)-ones Containing Fully Substituted Quaternary Stereogenic Center." Catalysts 9, no. 2 (February 20, 2019): 192. http://dx.doi.org/10.3390/catal9020192.

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A highly efficient and enantioselective approach to the synthesis of functionalized benzofuran-3(2H)-ones is presented. It proceeds via an intramolecular Stetter reaction using β,β-disubstituted Michael acceptors in the construction of five-membered rings with fully-substituted quaternary stereogenic centers and is promoted by terpene-derived triazolium salts. As a result, a series of chiral 2,2-disubstituted benzofuran-3(2H)-one derivatives with linear, branched, and cyclic aliphatic substitutions on the quaternary stereogenic center were obtained in high yields and with excellent enantioselectivities of up to 99% ee.

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3

Yang, Mengchen, Chen Chen, Xing Yi, Yuan Li, Xiaoqin Wu, Qingshan Li, and Shurong Ban. "Thiosquaramide-catalysed asymmetric double Michael addition of 2-(3H)-furanones to nitroolefines." Organic & Biomolecular Chemistry 17, no. 11 (2019): 2883–86. http://dx.doi.org/10.1039/c9ob00330d.

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4

Jakhar, Ajay, Prathibha Kumari, Mohd Nazish, Noor-ul H. Khan, Rukhsana I. Kureshy, Sayed H. R. Abdi, and E. Suresh. "Catalytic asymmetric synthesis of enantioenriched β-nitronitrile bearing a C-CF3 stereogenic center." RSC Advances 6, no. 36 (2016): 29977–82. http://dx.doi.org/10.1039/c6ra00093b.

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5

Liu, Ming-Qing, Tao Jiang, Wen-Wen Chen, and Ming-Hua Xu. "Highly enantioselective Rh/chiral sulfur-olefin-catalyzed arylation of alkyl-substituted non-benzofused cyclic N-sulfonyl ketimines." Organic Chemistry Frontiers 4, no. 11 (2017): 2159–62. http://dx.doi.org/10.1039/c7qo00555e.

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6

Shimizu, Masahiro, Jun Kikuchi, Azusa Kondoh, and Masahiro Terada. "Chiral Brønsted acid-catalyzed intramolecular SN2′ reaction for enantioselective construction of a quaternary stereogenic center." Chemical Science 9, no. 26 (2018): 5747–57. http://dx.doi.org/10.1039/c8sc01942h.

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Construction of a quaternary stereogenic center was accomplished through the enantioselective intramolecular allylic substitution reaction of bis-trichloroacetimidate catalyzed by a chiral phosphoramide derivative.

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7

Štacko, Peter, Jos C. M. Kistemaker, and Ben L. Feringa. "Fluorine-Substituted Molecular Motors with a Quaternary Stereogenic Center." Chemistry - A European Journal 23, no. 27 (May 2, 2017): 6643–53. http://dx.doi.org/10.1002/chem.201700581.

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8

Liu, Yao, and Honggen Wang. "Unified enantioselective total syntheses of (−)-scholarisine G, (+)-melodinine E, (−)-leuconoxine and (−)-mersicarpine." Chemical Communications 55, no. 24 (2019): 3544–47. http://dx.doi.org/10.1039/c8cc09949a.

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A unified strategy enabled the enantioselective syntheses of (−)-scholarisine G, (+)-melodinine E, (−)-leuconoxine and (−)-mersicarpine from a common 2-alkylated indole bearing an all-carbon quaternary stereogenic center.

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9

Gui, Hou-Ze, Yin Wei, and Min Shi. "Construction of spirothioureas having an amino quaternary stereogenic center via a [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates." Organic & Biomolecular Chemistry 16, no. 47 (2018): 9218–22. http://dx.doi.org/10.1039/c8ob02748j.

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A [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates was disclosed, affording the corresponding spirocyclic oxindoles containing a spirothiourea structure and an amino quaternary stereogenic center in good to excellent yields.

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10

Wu, Xiao-Yun, Hou-Ze Gui, Harish Jangra, Yin Wei, Hendrik Zipse, and Min Shi. "Phosphine-catalyzed [3 + 2] annulation of 2-aminoacrylates with allenoates and mechanistic studies." Catalysis Science & Technology 10, no. 12 (2020): 3959–64. http://dx.doi.org/10.1039/d0cy00092b.

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A phosphine catalyzed formal [3 + 2] annulation was disclosed, affording 3-pyrrolines containing an amino quaternary stereogenic center in good to excellent yields. The catalytic mechanism was investigated by DFT and kinetic studies.

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11

Ruch, Marie, Nicolas Brach, Roméric Galéa, Patrick Wagner, and Gaëlle Blond. "Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis." Molecules 25, no. 21 (October 27, 2020): 4976. http://dx.doi.org/10.3390/molecules25214976.

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We report herein an efficient synthesis of furopyran derivatives through a gold(I)-catalyzed domino reaction. The cascade reaction starts with two regioselective cyclizations, a 5-endo-dig and a 8-endo-dig, followed with a Grob-type fragmentation and a hetero Diels–Alder. The obtained furopyran derivatives contain fused and spiro-heterocycles. During this one-pot process, four bonds and four controlled stereogenic centers including a quaternary center are formed.

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12

Yao, Lu, and Kazuaki Ishihara. "Enantioselective [1,3] O-to-C rearrangement: dearomatization of alkyl 2-allyloxy/benzyloxy-1/3-naphthoates catalyzed by a chiral π–Cu(ii) complex." Chemical Science 10, no. 8 (2019): 2259–63. http://dx.doi.org/10.1039/c8sc05601c.

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An asymmetric [1,3] O-to-C rearrangement of alkyl 2-allyloxy/benzyloxy-1/3-naphthoates was realized under the catalysis of a chiral π–Cu(ii) complex to produce naphthalenone derivatives bearing an all-carbon quaternary stereogenic center in good to high yield with excellent enantioselectivity. The π–cation interaction of the complex was proved by X-ray diffraction analysis.

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13

Enders, Dieter, Andrea Zamponi, Gerhard Raabe, and Jan Runsink. "Enantioselective Synthesis of 2-Alkyl-2-cyanocycloalkanones with a Quaternary Stereogenic Center." Synthesis 1993, no. 07 (1993): 725–28. http://dx.doi.org/10.1055/s-1993-25929.

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14

Enders, Dieter, Andreas Zamponi, Thomas Schäfer, Christoph Nübling, Herbert Eichenauer, Ayhan Sitki Demir, and Gerhard Raabe. "Enantioselective Synthesis of Polyfunctional Small Building Blocks with a Quaternary Stereogenic Center." Chemische Berichte 127, no. 9 (September 1994): 1707–21. http://dx.doi.org/10.1002/cber.19941270922.

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15

De Fusco, Claudia, Tiziana Fuoco, Gianluca Croce, and Alessandra Lattanzi. "Noncovalent Organocatalytic Synthesis of Enantioenriched Terminal Aziridines with a Quaternary Stereogenic Center." Organic Letters 14, no. 16 (August 2, 2012): 4078–81. http://dx.doi.org/10.1021/ol3017066.

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16

Nakazawa, Koichi, Masaki Hayashi, Masakazu Tanaka, Mariko Aso, and Hiroshi Suemune. "Introduction of a quaternary stereogenic center to oxindole using cholinesterase-catalyzed asymmetric hydrolysis." Tetrahedron: Asymmetry 12, no. 6 (April 2001): 897–901. http://dx.doi.org/10.1016/s0957-4166(01)00138-0.

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17

Fukuda, Yu-ichi, Hiroyuki Sasaki, Mitsuru Shindo, and Kozo Shishido. "Diastereoselective ring-closing metathesis for the construction of a quaternary carbon stereogenic center." Tetrahedron Letters 43, no. 11 (March 2002): 2047–49. http://dx.doi.org/10.1016/s0040-4039(02)00162-4.

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18

Xie, Chen, Wanxing Sha, Yi Zhu, Jianlin Han, Vadim A. Soloshonok, and 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, no. 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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19

Luo, Chaosheng, and Yong Huang. "A Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines: Quaternary Stereogenic Center Inversion and Functionalization." Journal of the American Chemical Society 135, no. 22 (May 21, 2013): 8193–96. http://dx.doi.org/10.1021/ja4040945.

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20

Drelich, Piotr, Anna Skrzyńska, and Łukasz Albrecht. "Asymmetric Synthesis of β-Amino-α-hydroxy Aldehyde Derivatives Bearing a Quaternary Stereogenic Center." European Journal of Organic Chemistry 2016, no. 25 (August 15, 2016): 4302–6. http://dx.doi.org/10.1002/ejoc.201600872.

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21

De Fusco, Claudia, Tiziana Fuoco, Gianluca Croce, and Alessandra Lattanzi. "ChemInform Abstract: Noncovalent Organocatalytic Synthesis of Enantioenriched Terminal Aziridines with a Quaternary Stereogenic Center." ChemInform 43, no. 50 (November 29, 2012): no. http://dx.doi.org/10.1002/chin.201250100.

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22

ENDERS, D., A. ZAMPONI, G. RAABE, and J. RUNSINK. "ChemInform Abstract: Enantioselective Synthesis of 2-Alkyl-2-cyanocycloalkanones with a Quaternary Stereogenic Center." ChemInform 25, no. 15 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199415058.

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23

ENDERS, D., A. ZAMPONI, T. SCHAEFER, C. NUEBLING, H. EICHENAUER, A. S. DEMIR, and G. RAABE. "ChemInform Abstract: Enantioselective Synthesis of Polyfunctional Small Building Blocks with a Quaternary Stereogenic Center." ChemInform 26, no. 6 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199506046.

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24

Ge, Haihong, Shuang Liu, Yan Cai, Zenghui Gao, Siyi Du, Zhiwei Miao, and Guixian Xie. "Diastereoselective [Cu(MeCN)4BF4/BF3·Et2O]-Catalyzed Cyclopropenation of Alkynes: Asymmetric Synthesis of β-Amino-α-cyclopropenyl Phosphonates." SynOpen 01, no. 01 (March 2017): 0068–75. http://dx.doi.org/10.1055/s-0036-1590969.

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The diastereospecific formation of β-amino-α-cyclopropenyl phosphonates has been achieved in moderate yields from the cyclopropenation of 1-alkynes with dialkyl α-diazophosphonates. The reaction was performed by using a combined catalyst consisting of Cu(MeCN)4BF4 and BF3·Et2O as additive in dichloromethane at 40 °C. A possible mechanism for the reaction has been proposed to explain the origin of the activation and the asymmetric induction. This method provides a versatile approach to β-amino-α-cyclopropenylphosphonates containing a quaternary stereogenic center with good efficiency and diastereoselectivity.

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25

Rodríguez-Rodríguez, Jesús A., Vicente Gotor, and Rosario Brieva. "Lipase catalyzed resolution of the quaternary stereogenic center in ketone-derived benzo-fused cyclic cyanohydrins." Tetrahedron: Asymmetry 22, no. 11 (June 2011): 1218–24. http://dx.doi.org/10.1016/j.tetasy.2011.07.004.

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26

Kawato, Yuji, Noriko Takahashi, Naoya Kumagai, and Masakatsu Shibasaki. "Catalytic Asymmetric Conjugate Addition of α-Cyanoketones for the Construction of a Quaternary Stereogenic Center." Organic Letters 12, no. 7 (April 2, 2010): 1484–87. http://dx.doi.org/10.1021/ol100183s.

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27

Inokoishi, Yogo, Niiha Sasakura, Keiji Nakano, Yoshiyasu Ichikawa, and Hiyoshizo Kotsuki. "A New Powerful Strategy for the Organocatalytic Asymmetric Construction of a Quaternary Carbon Stereogenic Center." Organic Letters 12, no. 7 (April 2, 2010): 1616–19. http://dx.doi.org/10.1021/ol100350w.

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28

Fukuda, Yu-ichi, Hiroyuki Sasaki, Mitsuru Shindo, and Kozo Shishido. "ChemInform Abstract: Diastereoselective Ring-Closing Metathesis for the Construction of a Quaternary Carbon Stereogenic Center." ChemInform 33, no. 27 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200227077.

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29

Vaithiyanathan, Venkataramasubramanian, Mun Jong Kim, Yidong Liu, Hailong Yan, and Choong Eui Song. "Direct Access to Chiral β-Fluoroamines with Quaternary Stereogenic Center through Cooperative Cation-Binding Catalysis." Chemistry - A European Journal 23, no. 6 (December 22, 2016): 1268–72. http://dx.doi.org/10.1002/chem.201605637.

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30

Liu, Kang, Huai-Long Teng, Lu Yao, Hai-Yan Tao, and Chun-Jiang Wang. "Silver-Catalyzed Enantioselective Desymmetrization: Facile Access to Spirolactone-Pyrrolidines Containing a Spiro Quaternary Stereogenic Center." Organic Letters 15, no. 9 (April 23, 2013): 2250–53. http://dx.doi.org/10.1021/ol400821q.

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31

Nakazawa, Koichi, Masaki Hayashi, Masakazu Tanaka, Mariko Aso, and Hiroshi Suemune. "ChemInform Abstract: Introduction of a Quaternary Stereogenic Center to Oxindole Using Cholinesterase-Catalyzed Asymmetric Hydrolysis." ChemInform 32, no. 37 (May 24, 2010): no. http://dx.doi.org/10.1002/chin.200137125.

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32

Preshel-Zlatsin, Maya, Fa-Guang Zhang, Guillaume Eppe, and Ilan Marek. "Formation of Carbon Quaternary Stereogenic Center in Acyclic Systems via a Sequence of Carbometalation–Intramolecular Cyclization–Silicon Activation." Synthesis 48, no. 19 (June 10, 2016): 3279–86. http://dx.doi.org/10.1055/s-0035-1561666.

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The diastereoselective carbometalation reaction of cyclopropenyl esters followed by reaction with acylsilanes provides γ-silylated lactones that undergo a ‘sila-Grob’ fragmentation to give pyrone enolates as a new source of acyclic δ-diketones, δ-keto acid, and δ-keto ester derivatives possessing a quaternary stereocenter.

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33

Cramer, Nicolai, and Tobias Seiser. "β-Carbon Elimination from Cyclobutanols: A Clean Access to Alkylrhodium Intermediates Bearing a Quaternary Stereogenic Center." Synlett 2011, no. 04 (February 8, 2011): 449–60. http://dx.doi.org/10.1055/s-0030-1259536.

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34

Komine, Keita, Yasuhiro Urayama, Taku Hosaka, Hayato Fukuda, Susumi Hatakeyama, and Jun Ishihara. "New entry to the enantioselective formation of substituted cyclohexenes bearing an all‐carbon quaternary stereogenic center." Chirality 32, no. 3 (January 20, 2020): 273–81. http://dx.doi.org/10.1002/chir.23173.

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35

Luo, Chaosheng, and Yong Huang. "ChemInform Abstract: A Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines: Quaternary Stereogenic Center Inversion and Functionalization." ChemInform 44, no. 48 (November 8, 2013): no. http://dx.doi.org/10.1002/chin.201348164.

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36

Pedro, José R., Carlos Vila, Laura Carceller-Ferrer, and Gonzalo Blay. "Recent Advances in Catalytic Enantioselective Synthesis of Pyrazolones with a Tetrasubstituted Stereogenic Center at the 4-Position." Synthesis 53, no. 02 (October 8, 2020): 215–37. http://dx.doi.org/10.1055/s-0040-1707298.

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AbstractPyrazolone [2,4-dihydro-3H-pyrazol-4-one] represents one of the most important five-membered nitrogen heterocycles which is present in numerous pharmaceutical drugs and molecules with biological activity. Recently, many catalytic methodologies for the asymmetric synthesis of chiral pyrazolones have been established with great success, specially, for the synthesis of pyrazolones bearing a tetrasubstituted stereocenter at C-4. This review summarizes these excellent research studies since 2018, including representative examples and some mechanistic pathways explaining the observed stereochemistry.1 Introduction2 Catalytic Enantioselective Synthesis of Chiral Pyrazolones with a Full Carbon Tetrasubstituted Stereocenter at C-43 Catalytic Enantioselective Synthesis of Chiral Pyrazolones with a Quaternary Carbon Stereocenter at C-4 bearing a Heteroatom4 Catalytic Enantioselective Synthesis of Chiral Spiropyrazolones5 Conclusion

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37

Lussier, Tommy, Amarender Manchoju, Gang Wang, Starr Dostie, Scott Foster, Philippe Mochirian, Michel Prévost, and Yvan Guindon. "Diastereoselective Synthesis of Arabino- and Ribo-like Nucleoside Analogues Bearing a Stereogenic C3′ All-Carbon Quaternary Center." Journal of Organic Chemistry 84, no. 24 (November 15, 2019): 16055–67. http://dx.doi.org/10.1021/acs.joc.9b02550.

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38

Fujita, Takuma, Kazuhiro Obata, Shunsuke Kuwahara, Nobuaki Miura, Atsufumi Nakahashi, Kenji Monde, John Decatur, and Nobuyuki Harada. "(R)-(+)-[VCD(+)945]-4-Ethyl-4-methyloctane, the simplest chiral saturated hydrocarbon with a quaternary stereogenic center." Tetrahedron Letters 48, no. 24 (June 2007): 4219–22. http://dx.doi.org/10.1016/j.tetlet.2007.04.079.

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39

Richter, Celin, Minh Nguyen Trung, and Rainer Mahrwald. "Multicomponent Cascade Reactions of Unprotected Ketoses and Amino Acids – Access to a Defined Configured Quaternary Stereogenic Center." Journal of Organic Chemistry 80, no. 21 (October 22, 2015): 10849–65. http://dx.doi.org/10.1021/acs.joc.5b02003.

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40

Becerril-Jiménez, Fabiola, Tommy Lussier, Louis Leblanc, Carla Eymard, Starr Dostie, Michel Prévost, and Yvan Guindon. "Photoredox-Catalyzed Stereoselective Radical Reactions to Synthesize Nucleoside Analogues with a C2′-Stereogenic All-Carbon Quaternary Center." Journal of Organic Chemistry 84, no. 22 (October 22, 2019): 14795–804. http://dx.doi.org/10.1021/acs.joc.9b02374.

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41

Penrose, Stephen D., Andrew J. Stott, Perla Breccia, Alan F. Haughan, Roland W. Bürli, Rebecca E. Jarvis, and Celia Dominguez. "Inter- and Intramolecular Annulation Strategies to a Cyclopentanone Building Block Containing an All-Carbon Quaternary Stereogenic Center." Organic Letters 17, no. 6 (February 27, 2015): 1401–4. http://dx.doi.org/10.1021/acs.orglett.5b00207.

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42

Kawato, Yuji, Noriko Takahashi, Naoya Kumagai, and Masakatsu Shibasaki. "ChemInform Abstract: Catalytic Asymmetric Conjugate Addition of α-Cyanoketones for the Construction of a Quaternary Stereogenic Center." ChemInform 41, no. 33 (July 24, 2010): no. http://dx.doi.org/10.1002/chin.201033026.

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43

Liu, Kang, Huai-Long Teng, Lu Yao, Hai-Yan Tao, and Chun-Jiang Wang. "ChemInform Abstract: Silver-Catalyzed Enantioselective Desymmetrization: Facile Access to Spirolactone-Pyrrolidines Containing a Spiro Quaternary Stereogenic Center." ChemInform 44, no. 35 (August 8, 2013): no. http://dx.doi.org/10.1002/chin.201335117.

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44

Russo, Alessio, Gerardina Galdi, Gianluca Croce, and Alessandra Lattanzi. "Highly Enantioselective Epoxidation Catalyzed by Cinchona Thioureas: Synthesis of Functionalized Terminal Epoxides Bearing a Quaternary Stereogenic Center." Chemistry - A European Journal 18, no. 20 (April 18, 2012): 6152–57. http://dx.doi.org/10.1002/chem.201200500.

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45

Simaan, Samah, Alexander F. G. Goldberg, Stephane Rosset, and Ilan Marek. "Metal-Catalyzed Ring-Opening of Alkylidenecyclopropanes: New Access to Building Blocks with an Acyclic Quaternary Stereogenic Center." Chemistry - A European Journal 16, no. 3 (November 30, 2009): 774–78. http://dx.doi.org/10.1002/chem.200902656.

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46

KOSAKA, T., T. BANDO, and K. SHISHIDO. "ChemInform Abstract: New Asymmetric Construction of the Benzylic Quaternary Stereogenic Center: An Enantiocontrolled Access to (-)-α-Cuparenone." ChemInform 28, no. 44 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199744272.

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47

Inokoishi, Yogo, Niiha Sasakura, Keiji Nakano, Yoshiyasu Ichikawa, and Hiyoshizo Kotsuki. "ChemInform Abstract: A New Powerful Strategy for the Organocatalytic Asymmetric Construction of a Quaternary Carbon Stereogenic Center." ChemInform 41, no. 34 (July 29, 2010): no. http://dx.doi.org/10.1002/chin.201034090.

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48

Tambutet, Guillaume, Fabiola Becerril-Jiménez, Starr Dostie, Ryan Simard, Michel Prévost, Philippe Mochirian, and Yvan Guindon. "Dual-Face Nucleoside Scaffold Featuring a Stereogenic All-Carbon Quaternary Center. Intramolecular Silicon Tethered Group-Transfer Reaction." Organic Letters 16, no. 21 (October 16, 2014): 5698–701. http://dx.doi.org/10.1021/ol502777r.

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49

Kang, Jun Yong, and Rich G. Carter. "Primary Amine, Thiourea-Based Dual Catalysis Motif for Synthesis of Stereogenic, All-Carbon Quaternary Center-Containing Cycloalkanones." Organic Letters 14, no. 12 (June 5, 2012): 3178–81. http://dx.doi.org/10.1021/ol301272r.

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50

Trancard, Delphine, Jean-Baptiste Tout, Thierry Giard, Ilhame Chichaoui, Dominique Cahard, and Jean-Christophe Plaquevent. "Pyrrolidines bearing a quaternary α-stereogenic center. Part 2: Access to proline chimeras, stereoselective approach and mechanistic aspects." Tetrahedron Letters 41, no. 20 (May 2000): 3843–47. http://dx.doi.org/10.1016/s0040-4039(00)00505-0.

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