Diastereomerically and Enantiomerically Pure 2,3-Disubstituted Pyrrolidines from 2,3-Aziridin-1-ols Using a Sulfoxonium Ylide:  A One-Carbon Homologative Relay Ring Expansion

Jennifer M. Schomaker, Somnath Bhattacharjee, Jun Yan, and Babak Borhan*
Contribution from the Department of Chemistry, Michigan State University, East Lansing, Michigan 48824
J. Am. Chem. Soc., 2007, 129 (7), pp 1996–2003
DOI: 10.1021/ja065833p
Publication Date (Web): January 27, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, borhan@cem.msu.edu

Abstract

Abstract Image

An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine, thus completing the relay of the three-membered to the five-membered nitrogen-containing ring system. This process takes place with complete transfer of stereochemical fidelity and can be applied to sterically hindered aziridinols.

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History

  • Published In Issue February 21, 2007
  • Received August 17, 2006

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