Tetrahedron

Chiral ligand-controlled asymmetric conjugate amination of enoates with lithium mesitylmethyl (trimethylsilyl) amide

T Sakai, H Doi, K Tomioka

Index: Sakai, Takeo; Doi, Hirohisa; Tomioka, Kiyoshi Tetrahedron, 2006 , vol. 62, # 35 p. 8351 - 8359

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Citation Number: 25

Abstract

Lithium mesitylmethyl (trimethylsilyl) amide behaved as a nice amination agent in a chiral ligand-controlled conjugate addition reaction of tert-butyl cinnamate to give the conjugate amination product with 99% ee in 90% yield. Other acyclic and cyclic enoates were also aminated in reasonably high enantioselectivity, while the deprotonation of abstractable proton of enoates caused yield loss of the conjugate amination products, due to the ...