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Diastereoselective Synthesis of α-Quaternary Aziridine-2-carboxylates via Aza-Corey-Chaykovsky Aziridination of N-tert-Butanesulfinyl Ketimino Esters

Maurice A. Marsini*, Jonathan T. Reeves, Jean-Nicolas Desrosiers, Melissa A. Herbage, Jolaine Savoie, Zhibin Li, Keith R. Fandrick, C. Avery Sader, Bryan McKibben, Donghong A. Gao, Jianwen Cui, Nina C. Gonnella, Heewon Lee, Xudong Wei, Frank Roschangar, Bruce Z. Lu and Chris H. Senanayake

*Departments of Chemical Development and Medicinal Chemistry, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States, Email: maurice.marsiniboehringer-ingelheim.com

M. A. Marsini, J. T. Reeves, J.-N. Desrosiers, M. A. Herbage, J. Savoie, Z. Li, K. R. Fandrick, C. A. Sader, B. McKibben, D. A. Gao, J. Cui, N. C. Gonnella, H. Lee, X. Wei, F. Roschangar, B. Z. Lu, C. H. Senanayake, Org. Lett., 2015, 17, 5614-5617.

DOI: 10.1021/acs.orglett.5b02838 (free Supporting Information)


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Abstract

A general, scalable, and highly diastereoselective aziridination of N-tert-butanesulfinyl ketimino esters provides straightforward access to previously unobtainable, biologically relevant α-quaternary amino esters and derivatives starting from readily available precursors.

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Key Words

Corey-Chaykovsky Reaction


ID: J54-Y2015