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Paper | Special issue | Vol 77, No. 2, 2009, pp.927-943
Published online, 2nd October, 2008
DOI: 10.3987/COM-08-S(F)102
Chirality Control of Tropos Diphenylmethane-derived Phosphoramidites by Chiral Dienes: Its Application to Asymmetric Michael Addition

Kazuki Wakabayashi, Kohsuke Aikawa, and Koichi Mikami*

*Department of Applied Chemistry, Graduate School of Science and Technology, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan

Abstract

The Rh complex of tropos diphenylmethane-derived phosphoramidite could be chirally controlled to adopt single chiral conformation upon addition of a chiral diene. In the asymmetric Michael addition of α-cyanocarboxylates catalyzed by the Rh complexes, the chiral diene and bisphenylmethane-derived phosphoramidite functioned to attain higher enantioselectivity and catalytic activity via asymmetric activation.