Diastereomerically and enantiomerically pure 2, 3-disubstituted pyrrolidines from 2, 3-aziridin-1-ols using a sulfoxonium ylide: a one-carbon homologative relay ring …

JM Schomaker, S Bhattacharjee, J Yan…

Index: Schomaker, Jennifer M.; Bhattacharjee, Somnath; Yan, Jun; Borhan, Babak Journal of the American Chemical Society, 2007 , vol. 129, # 7 p. 1996 - 2003

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Citation Number: 62

Abstract

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- ...