Premium
Enantioselective Synthesis of Chiral 3‐Substituted‐3‐silylpropionic Esters via Rhodium/Bisphosphine‐Thiourea‐Catalyzed Asymmetric Hydrogenation
Author(s) -
Zhang Zongpeng,
Han Zhengyu,
Gu Guoxian,
Dong XiuQin,
Zhang Xumu
Publication year - 2017
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.201700355
Subject(s) - chemistry , rhodium , enantioselective synthesis , asymmetric hydrogenation , thiourea , catalysis , yield (engineering) , organic chemistry , silylation , materials science , metallurgy
We have successfully developed the asymmetric hydrogenation of β‐silyl‐α,β‐unsaturated esters to prepare chiral 3‐substituted‐3‐silylpropionic ester products catalyzed by rhodium/bisphosphine‐thiourea (ZhaoPhos) with excellent results (up to 97% yield, >99% ee , 1500 TON). Moreover, our hydrogenation products can be efficiently converted to other important organic molecules, such as chiral ethyl ( R )‐3‐hydroxy‐3‐phenylpropanoate or ( R )‐3‐[dimethyl(phenyl)silyl]‐3‐phenylpropanoic acid.