Development of chiral (S)-prolinol-derived ligands for palladium-catalyzed asymmetric allylic alkylation: effect of a siloxymethyl group on the pyrrolidine backbone.
A series of novel chiral aminophosphine ligands are designed and readily prepared from (S)-prolinol. The reactivity and selectivity in the palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with a dimethyl malonate-BSA-LiOAc system using these chiral ligands are evaluated, and the structural elucidation of ligands and palladium complex is also conducted. Moreover, a series of trialkylsilylated chiral aminophosphine ligands are prepared and applied to palladium-catalyzed asymmetric allylic alkylation (up to 98% ee).
Tanaka
Youichi
Y
Department of Materials Technology, Faculty of Engineering, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
Mino
Takashi
T
Akita
Koji
K
Sakamoto
Masami
M
Fujita
Tsutomu
T