Premium
Enantioselective Cyanosilylation of Ketones Catalyzed by a Nitrogen‐Containing Bifunctional Catalyst
Author(s) -
Xiong Yan,
Huang Xiao,
Gou Shaohua,
Huang Jinglun,
Wen Yuehong,
Feng Xiaoming
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505418
Subject(s) - enantioselective synthesis , chemistry , bifunctional , pyrrolidine , catalysis , trimethylsilyl cyanide , bifunctional catalyst , ligand (biochemistry) , cyanohydrin , cyanide , organic chemistry , medicinal chemistry , biochemistry , receptor
An efficient and optically active, bifunctional tetraaza ligand (2 S )‐ N ‐{(1 R ,2 R )‐2‐[( S )‐pyrrolidine‐2‐carboxamido]‐1,2‐diphenylethyl}pyrrolidine‐2‐carboxamide has been developed for the addition of trimethylsilyl cyanide (TMSCN) to ketones. The bifunctional catalyst system based on a monometallic titanium complex was found to be a highly enantioselective catalyst to provide O ‐TMS cyanohydrins with up to 94% ee. A possible transition state has been proposed to explain the origin of the activation and asymmetric inductivity.