Org Lett. 2008 May 1;10(9):1747-50. Epub 2008 Mar 29.

Highly enantioselective asymmetric 1,3-dipolar cycloaddition of azomethine ylide catalyzed by a copper(I)/ClickFerrophos complex.

Source

Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, Tokyo, Japan. fukuzawa@chem.chuo-u.ac.jp

Abstract

A copper(I)/ClickFerrophos complex catalyzed the asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with vinyl sulfone to give the exo-2,4,5-trisubstituted pyrrolidine in good yield with high enantioselectivity (99% ee). The complex also effectively catalyzed reactions of other dipolarophiles such as acrylates, maleate, and maleimides to give the exo-2,4,5-, and 2,3,4,5-substituted pyrrolidine derivatives with high diastereo- and enantioselectivities.

PMID:: 18373347; [PubMed - indexed for MEDLINE]

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