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.
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.
see article for more examples
S.-i. Fukuzawa, H. Oki, Org. Lett., 2008, 10, 1747-1750.