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Journal articles on the topic 'Spiroaminals'

Author: Grafiati

Published: 2 June 2025

Last updated: 31 July 2025

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1

Sinibaldi, Marie-Eve, and Isabelle Canet. "Synthetic Approaches to Spiroaminals." European Journal of Organic Chemistry 2008, no. 26 (2008): 4391–99. http://dx.doi.org/10.1002/ejoc.200800371.

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2

Kumar, Rayala Naveen, and Seongmin Lee. "Hypervalent Iodine-Mediated Synthesis of Steroidal 5/5-Spiroiminals." Molecules 29, no. 23 (2024): 5812. https://doi.org/10.3390/molecules29235812.

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The hypervalent iodine-mediated formation of steroidal 5/5-spiroiminals and 5/5-spiroaminals from steroidal amines is presented. Under the influence of excess PhI(OAc)2 and iodine in acetonitrile at 0 °C, steroidal amines smoothly underwent cyclization to give a mixture of 5/5-spiroiminals and 5/5-spiroaminals. This reaction represents the first example of a C-H-activation-mediated formation of a spiroiminal. Presumably, the formation of 5/5-spiroiminals occurs through aminyl radical-mediated cyclization followed by amine-to-imine oxidation.

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3

Zhang, Shuo, Zhengliang Xu, Jiong Jia, Chen-Ho Tung, and Zhenghu Xu. "Synthesis of spiroaminals by bimetallic Au/Sc relay catalysis: TMS as a traceless controlling group." Chem. Commun. 50, no. 81 (2014): 12084–87. http://dx.doi.org/10.1039/c4cc05610h.

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4

Almond-Thynne, Joshua, Andrew J. P. White, Anastasios Polyzos, Henry S. Rzepa, Philip J. Parsons, and Anthony G. M. Barrett. "Synthesis and Reactions of Benzannulated Spiroaminals: Tetrahydrospirobiquinolines." ACS Omega 2, no. 7 (2017): 3241–49. http://dx.doi.org/10.1021/acsomega.7b00482.

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5

Wang, Xianghua, Shuli Dong, Zhili Yao, et al. "Synthesis of Spiroaminals and Spiroketals with Bimetallic Relay Catalysis." Organic Letters 16, no. 1 (2013): 22–25. http://dx.doi.org/10.1021/ol4033286.

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6

John Pal, Adabala Pal, Parasuraman Kadigachalam, Asadulla Mallick, Venkata Ramana Doddi, and Yashwant D. Vankar. "Synthesis of sugar-derived spiroaminals via lactamization and metathesis reactions." Org. Biomol. Chem. 9, no. 3 (2011): 809–19. http://dx.doi.org/10.1039/c0ob00555j.

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7

Boonlarppradab, Chollaratt, Christopher A. Kauffman, Paul R. Jensen, and William Fenical. "Marineosins A and B, Cytotoxic Spiroaminals from a Marine-Derived Actinomycete." Organic Letters 10, no. 24 (2008): 5505–8. http://dx.doi.org/10.1021/ol8020644.

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8

Wang, Xianghua, Shuli Dong, Zhili Yao, et al. "ChemInform Abstract: Synthesis of Spiroaminals and Spiroketals with Bimetallic Relay Catalysis." ChemInform 45, no. 22 (2014): no. http://dx.doi.org/10.1002/chin.201422147.

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9

Loerbroks, Claudia, Birte Böker, Jens Cordes, Anthony G. M. Barrett, and Walter Thiel. "Spiroaminals - Crystal Structure and Computational Investigation of Conformational Preferences and Tautomerization Reactions." European Journal of Organic Chemistry 2014, no. 25 (2014): 5476–86. http://dx.doi.org/10.1002/ejoc.201402576.

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10

John Pal, A. P., and Yashwant D. Vankar. "Azidation of anomeric nitro sugars: application in the synthesis of spiroaminals as glycosidase inhibitors." Tetrahedron Letters 51, no. 18 (2010): 2519–24. http://dx.doi.org/10.1016/j.tetlet.2010.03.003.

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11

Gong, Jun, Qian Wan, and Qiang Kang. "Gold(I)/Chiral Rh(III) Lewis Acid Relay Catalysis Enables Asymmetric Synthesis of Spiroketals and Spiroaminals." Advanced Synthesis & Catalysis 360, no. 21 (2018): 4031–36. http://dx.doi.org/10.1002/adsc.201800492.

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12

Zhang, Shuo, Zhengliang Xu, Jiong Jia, Chen-Ho Tung, and Zhenghu Xu. "ChemInform Abstract: Synthesis of Spiroaminals by Bimetallic Au/Sc Relay Catalysis: TMS as a Traceless Controlling Group." ChemInform 46, no. 11 (2015): no. http://dx.doi.org/10.1002/chin.201511122.

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13

Yang, Yuhuan, and Senmiao Xu. "A Versatile Enantioselective Catalytic Cyclopropanation-Rearrangement Approach to the Divergent Construction of Chiral Spiroaminals and Fused Bicyclic Acetals." Chinese Journal of Organic Chemistry 40, no. 12 (2020): 4380. http://dx.doi.org/10.6023/cjoc202000089.

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14

Yang, Yuhuan, and Senmiao Xu. "A Versatile Enantioselective Catalytic Cyclopropanation-Rearrangement Approach to the Divergent Construction of Chiral Spiroaminals and Fused Bicyclic Acetals." Chinese Journal of Organic Chemistry 40, no. 12 (2020): 4380. http://dx.doi.org/10.6023/cjoc202000089.

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15

Zhou, Li, Wen‐Guang Yan, Xiu‐Li Sun, Lijia Wang, and Yong Tang. "A Versatile Enantioselective Catalytic Cyclopropanation‐Rearrangement Approach to the Divergent Construction of Chiral Spiroaminals and Fused Bicyclic Acetals." Angewandte Chemie 132, no. 43 (2020): 19126–31. http://dx.doi.org/10.1002/ange.202007068.

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16

Zhou, Li, Wen‐Guang Yan, Xiu‐Li Sun, Lijia Wang, and Yong Tang. "A Versatile Enantioselective Catalytic Cyclopropanation‐Rearrangement Approach to the Divergent Construction of Chiral Spiroaminals and Fused Bicyclic Acetals." Angewandte Chemie International Edition 59, no. 43 (2020): 18964–69. http://dx.doi.org/10.1002/anie.202007068.

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17

Harada, Shingo, Mayu Kobayashi, Masato Kono, and Tetsuhiro Nemoto. "Site-Selective and Chemoselective C–H Functionalization for the Synthesis of Spiroaminals via a Silver-Catalyzed Nitrene Transfer Reaction." ACS Catalysis 10, no. 22 (2020): 13296–304. http://dx.doi.org/10.1021/acscatal.0c04057.

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18

Li, Jun, Lili Lin, Bowen Hu, et al. "Bimetallic Gold(I)/Chiral N ,N′ -Dioxide Nickel(II) Asymmetric Relay Catalysis: Chemo- and Enantioselective Synthesis of Spiroketals and Spiroaminals." Angewandte Chemie International Edition 55, no. 20 (2016): 6075–78. http://dx.doi.org/10.1002/anie.201601701.

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19

Li, Jun, Lili Lin, Bowen Hu, et al. "Bimetallic Gold(I)/Chiral N ,N′ -Dioxide Nickel(II) Asymmetric Relay Catalysis: Chemo- and Enantioselective Synthesis of Spiroketals and Spiroaminals." Angewandte Chemie 128, no. 20 (2016): 6179–82. http://dx.doi.org/10.1002/ange.201601701.

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20

Gong, Jun, Qian Wan, and Qiang Kang. "Front Cover Picture: Gold(I)/Chiral Rh(III) Lewis Acid Relay Catalysis Enables Asymmetric Synthesis of Spiroketals and Spiroaminals (Adv. Synth. Catal. 21/2018)." Advanced Synthesis & Catalysis 360, no. 21 (2018): 4029. http://dx.doi.org/10.1002/adsc.201800884.

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21

Karger, Kerstin, Katharina Bechthold, and Gerhard Maas. "Derivatives of the triaminoguanidinium ion, 7: unsymmetrically substituted N,N',N''-triaminoguanidinium salts via a cyclopentanone spiroaminal intermediate." Zeitschrift für Naturforschung B 75, no. 6-7 (2020): 517–28. http://dx.doi.org/10.1515/znb-2020-0004.

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AbstractN,N′,N″-Triaminoguanidinium chloride (TAG-Cl) reacts with cyclopentanone or cyclohexanone to afford 8-(2-cyclopentylidenehydrazinyl)-6,7,9,10-tetraazaspiro[4.5]decan-8-ylium and 3-(2-cyclohexylidenehydrazinyl)-1,2,4,5-tetraazaspiro[5,5]undecan-3-ylium salts, respectively, i. e., two arms of the TAG ion were engaged in spiroaminal formation and the NH2 group of the third arm underwent imine-forming condensation. Ring-opening reactions of the cyclopentanone derived spiroaminal with aldehydes, aryl ketones, aromatic or aliphatic isocyanates give access to a variety of unsymmetrically subs

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22

Zhang, Li-Hua, Bao-Min Feng, Gang Chen, et al. "Sporulaminals A and B: a pair of unusual epimeric spiroaminal derivatives from a marine-derived fungus Paraconiothyrium sporulosum YK-03." RSC Advances 6, no. 48 (2016): 42361–66. http://dx.doi.org/10.1039/c6ra01401a.

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23

Nguyen, Son, Jianyan Xu, and Craig J. Forsyth. "Facile biomimetic syntheses of the azaspiracid spiroaminal." Tetrahedron 62, no. 22 (2006): 5338–46. http://dx.doi.org/10.1016/j.tet.2006.01.112.

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24

Panarese, Joseph D., Leah C. Konkol, Cynthia B. Berry, Brittney S. Bates, Leslie N. Aldrich, and Craig W. Lindsley. "Spiroaminal model systems of the marineosins with final step pyrrole incorporation." Tetrahedron Letters 54, no. 18 (2013): 2231–34. http://dx.doi.org/10.1016/j.tetlet.2013.02.059.

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25

Yamada, Takeshi, Tetsuya Ideguchi-Matsushita, Tomoyasu Hirose, et al. "Asymmetric Total Synthesis of Indole Alkaloids Containing an Indoline Spiroaminal Framework." Chemistry - A European Journal 21, no. 33 (2015): 11855–64. http://dx.doi.org/10.1002/chem.201501150.

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26

Sunazuka, Toshiaki, Tatsuya Shirahata, Satoshi Tsuchiya, et al. "A Concise Stereoselective Route to the Indoline Spiroaminal Framework of Neoxaline and Oxaline." Organic Letters 7, no. 5 (2005): 941–43. http://dx.doi.org/10.1021/ol050077y.

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27

Gueyrard, David. "Extension of the Modified Julia Olefination on Carboxylic Acid Derivatives: Scope and Applications." Synlett 29, no. 01 (2017): 34–45. http://dx.doi.org/10.1055/s-0036-1590916.

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This account relates our work in the field of modified Julia olefination to extend this very useful olefination method to carboxylic acid derivatives. Since our preliminary results on lactones in 2005, the reaction has been extended to a large range of derivatives (lactams, imides and anhydrides) through an intra- or intermolecular process leading to a great variety of structures (enol ethers, enamides and exo enol esters). This article will also focus on the application of this methodology for the preparation of biologically interesting compounds and/or total syntheses of natural products suc

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28

Middleton, Donald S., Nigel S. Simpkins, and Nicholas K. Terrett. "Synthesis of N-protected spiroamines related to natural products using radical cyclisations." Tetrahedron Letters 30, no. 29 (1989): 3865–68. http://dx.doi.org/10.1016/s0040-4039(01)80679-1.

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29

Qi, Zhongyu, Zhijie Zhang, Li Yang, et al. "Nitrogen‐Radical‐Triggered Trifunctionalizing ipso ‐Spirocyclization of Unactivated Alkenes with Vinyl Azides: A Modular Access to Spiroaminal Frameworks." Advanced Synthesis & Catalysis 363, no. 15 (2021): 3762–68. http://dx.doi.org/10.1002/adsc.202100517.

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30

Aldrich, Leslie N., Cynthia B. Berry, Brittney S. Bates, Leah C. Konkol, Miranda So, and Craig W. Lindsley. "Towards the Total Synthesis of Marineosin A: Construction of the Macrocyclic Pyrrole and an Advanced, Functionalized Spiroaminal Model." European Journal of Organic Chemistry 2013, no. 20 (2013): 4215–18. http://dx.doi.org/10.1002/ejoc.201300643.

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31

Culbertson, Townley P., Joseph P. Sanchez, Laura Gambino, and Josephine A. Sesnie. "Quinolone antibacterial agents substituted at the 7-position with spiroamines. Synthesis and structure-activity relationships." Journal of Medicinal Chemistry 33, no. 8 (1990): 2270–75. http://dx.doi.org/10.1021/jm00170a035.

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32

Gigant, Nicolas, Samuel Habib, Marie Medoc, Peter G. Goekjian, David Gueyrard, and Isabelle Gillaizeau. "Synthesis ofexo-Enamides from Protected Lactams Using a Modified Julia Olefination Reaction: Application to the Synthesis of Spiroaminal Fragments." European Journal of Organic Chemistry 2014, no. 29 (2014): 6501–6. http://dx.doi.org/10.1002/ejoc.201402681.

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33

CULBERTSON, T. P., J. P. SANCHEZ, L. GAMBINO, and J. A. SESNIE. "ChemInform Abstract: Quinolone Antibacterial Agents Substituted at the 7-Position with Spiroamines. Synthesis and Structure-Activity Relationships." ChemInform 22, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.199105217.

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34

Gigant, Nicolas, Samuel Habib, Marie Medoc, Peter G. Goekjian, David Gueyrard, and Isabelle Gillaizeau. "ChemInform Abstract: Synthesis of exo-Enamides from Protected Lactams Using a Modified Julia Olefination Reaction: Application to the Synthesis of Spiroaminal Fragments." ChemInform 46, no. 12 (2015): no. http://dx.doi.org/10.1002/chin.201512255.

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35

Kono, Masato, Shingo Harada, and Tetsuhiro Nemoto. "Rhodium-Catalyzed Stereospecific C−H Amination for the Construction of Spiroaminal Cores: Reactivity Difference between Nitrenoid and Carbenoid Species against Amide Functionality." Chemistry - A European Journal 23, no. 31 (2017): 7428–32. http://dx.doi.org/10.1002/chem.201701464.

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36

Gayen, Prasenjit, Suman Sar, and Prasanta Ghorai. "Stereodivergent Synthesis of Spiroaminals via Chiral Bifunctional Hydrogen Bonding Organocatalysis." Angewandte Chemie International Edition, April 2, 2024. http://dx.doi.org/10.1002/anie.202404106.

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Spiroaminals represent novel structural motifs prevalent in diverse natural products and biologically active molecules. Achieving their enantioselective synthesis is a highly desirable and challenging task in synthetic endeavors due to their intricate molecular frameworks. Herein, we accomplished the first stereodivergent construction of spiroaminals using chiral bifunctional organocatalyzed intramolecular 1,2‐addition followed by an oxa‐Michael addition cascade in a high atom and step economical pathway. A proper modulation of the cinchona‐derived squaramide catalysts efficiently provided acc

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37

Gayen, Prasenjit, Suman Sar, and Prasanta Ghorai. "Stereodivergent Synthesis of Spiroaminals via Chiral Bifunctional Hydrogen Bonding Organocatalysis." Angewandte Chemie, April 2, 2024. http://dx.doi.org/10.1002/ange.202404106.

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Spiroaminals represent novel structural motifs prevalent in diverse natural products and biologically active molecules. Achieving their enantioselective synthesis is a highly desirable and challenging task in synthetic endeavors due to their intricate molecular frameworks. Herein, we accomplished the first stereodivergent construction of spiroaminals using chiral bifunctional organocatalyzed intramolecular 1,2‐addition followed by an oxa‐Michael addition cascade in a high atom and step economical pathway. A proper modulation of the cinchona‐derived squaramide catalysts efficiently provided acc

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38

Dong, Min, Xi Lu, Sha Yu, et al. "Alkoxy Radical‐Triggered 1,1,2‐Trifunctionalization of Unactivated Alkenes towards N,O‐Spiroaminals." Chinese Journal of Chemistry, April 18, 2025. https://doi.org/10.1002/cjoc.70030.

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Comprehensive SummaryN,O‐Spiroaminals have potential biological activities and abilities to modulate the physicochemical and pharmacokinetic properties of drug molecules. However, effective catalytic methods for the efficient construction of N,O‐spiroaminals are still limited to date. Herein, we report a novel 1,1,2‐trifunctionalization of unactivated alkenes to rapidly and efficiently obtain a diverse array of architecturally intriguing N,O‐spiroaminals. This methodology exhibits broad substrate scope, good functional group compatibility, and potential synthetic utility by a scale‐up reaction

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39

Kalaitzakis, Dimitris, Eirini Antonatou, and Georgios Vassilikogiannakis. "One-pot synthesis of 1-azaspiro frameworks initiated by photooxidation of simple furans." October 24, 2013. https://doi.org/10.1039/C3CC47690A.

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A range of 1-azaspirocycles, spiroaminals and 1,6-diazaspirocycles has been synthesized, starting from simple and readily accessible furan precursors, using a cascade reaction sequence initiated by singlet oxygen.

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40

Sinibaldi, Marie-Eve, and Isabelle Canet. "ChemInform Abstract: Synthetic Approaches to Spiroaminals." ChemInform 39, no. 48 (2008). http://dx.doi.org/10.1002/chin.200848234.

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41

"Organocatalytic Stereodivergent Intramolecular Synthesis of Spiroaminals." Synfacts 20, no. 07 (2024): 0748. http://dx.doi.org/10.1055/s-0043-1775214.

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42

"Synthesis of Spiroaminals by Au/Sc Relay Catalysis." Synfacts 10, no. 11 (2014): 1138. http://dx.doi.org/10.1055/s-0034-1379352.

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43

"Gold/Iridium-Catalyzed Enantioselective Synthesis of Spiroketals and Spiroaminals." Synfacts 18, no. 07 (2022): 0725. http://dx.doi.org/10.1055/s-0041-1738222.

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44

"Spiroaminals and Fused Bicycles via an Enantioselective Cyclopropanation–Rearrangement Protocol." Synfacts 16, no. 10 (2020): 1189. http://dx.doi.org/10.1055/s-0040-1706432.

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45

"Spiroaminals and Spiroketals via Au/La and Au/Y Relay Catalysis." Synfacts 10, no. 03 (2014): 0240. http://dx.doi.org/10.1055/s-0033-1340806.

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46

Yang, Wu-Lin, Xin-Yu Shang, Xiaoyan Luo, and Wei-Ping Deng. "Enantioselective Synthesis of Spiroketals and Spiroaminals via Gold and Iridium Sequential Catalysis." Angewandte Chemie International Edition, April 21, 2022. http://dx.doi.org/10.1002/anie.202203661.

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47

Yang, Wu-Lin, Xin-Yu Shang, Xiaoyan Luo, and Wei-Ping Deng. "Enantioselective Synthesis of Spiroketals and Spiroaminals via Gold and Iridium Sequential Catalysis." Angewandte Chemie, April 21, 2022. http://dx.doi.org/10.1002/ange.202203661.

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48

Yang, Wu-Lin, Xin-Yu Shang, Tao Ni, et al. "Diastereo‐ and Enantioselective Synthesis of Bisbenzannulated Spiroketals and Spiroaminals by Ir/Ag/Acid Ternary Catalysis." Angewandte Chemie International Edition, August 3, 2022. http://dx.doi.org/10.1002/anie.202210207.

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49

Yang, Wu-Lin, Xin-Yu Shang, Tao Ni, et al. "Diastereo‐ and Enantioselective Synthesis of Bisbenzannulated Spiroketals and Spiroaminals by Ir/Ag/Acid Ternary Catalysis." Angewandte Chemie, August 3, 2022. http://dx.doi.org/10.1002/ange.202210207.

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50

Chen, Yang, Hui Yan, Hanliang Zheng, Wei-Ping Deng, Zhong Li, and Wu-Lin Yang. "Ir/Brønsted acid dual-catalyzed asymmetric synthesis of bisbenzannulated spiroketals and spiroaminals from isochroman ketals." Organic Chemistry Frontiers, 2024. http://dx.doi.org/10.1039/d4qo01402b.

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