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Highly Endo-Selective and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylide with α-Enones Catalyzed by a Silver(I)/ThioClickFerrophos Complex

Ichiro Oura, Kenta Shimizu, Kenichi Ogata and Shin-ichi Fukuzawa*

*Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan, Email: orgsynthkc.chuo-u.ac.jp

I. Oura, K. Shimizu, K. Ogata, S.-i. Fukuzawa, Org. Lett., 2010, 12, 1752-1755.

DOI: 10.1021/ol100336q (free Supporting Information)


Abstract

A highly endo-selective asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate as source of azomethine ylides with (E)-acyclic α-enones is catalyzed by a silver(I)/ThioClickFerrophos complex to give highly functionalized endo-4-acyl pyrrolidines in good yields with high enantioselectivities.

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Highly Enantioselective Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylide Catalyzed by a Copper(I)/ClickFerrophos Complex

S.-i. Fukuzawa, H. Oki, Org. Lett., 2008, 10, 1747-1750.


Key Words

1,3-dipolar cycloaddition, pyrrolidines


ID: J54-Y2010-1090