Highly endo-selective and enantioselective 1,3-dipolar cycloaddition of azomethine ylide with alpha-enones catalyzed by a silver(I)/ThioClickFerrophos complex.
A silver(I)/ThioClickFerrophos complex catalyzed the highly endo-selective asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with (E)-acyclic alpha-enones having an endo/exo ratio of 90/10 to 99/1. The highly functionalized endo-4-acyl pyrrolidines were obtained in good yields with high enantioselectivities (up to 98% ee). The complex also effectively catalyzed endo-selective reactions with 2-cyclopentenone to give the endo-bicyclic pyrrolidine in high enantioselectivity.
Oura
Ichiro
I
Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
Shimizu
Kenta
K
Ogata
Kenichi
K
Fukuzawa
Shin-Ichi
S