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Enantioselective Cyanosilylation of α,α‐Dialkoxy Ketones by Using Phosphine‐Thiourea Dual‐Reagent Catalysis
Author(s) -
Yu QiWen,
Wu LuPing,
Kang TianChen,
Xie Jin,
Sha Feng,
Wu XinYan
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800459
Subject(s) - enantioselective synthesis , chemistry , phosphine , bifunctional , thiourea , reagent , organic chemistry , catalysis , organocatalysis , combinatorial chemistry , bifunctional catalyst
The first highly enantioselective cyanosilylation of α,α‐dialkoxy ketones enabled by a dual‐reagent catalysis has been developed. With the combination of a chiral bifunctional phosphine‐thiourea and methyl acrylate, the key organophosphorus zwitterion intermediate was generated in situ as a novel Lewis base, which catalyzed the enantioselective cyanosilylation reaction in excellent yields (up to 99 %) with good‐to‐excellent enantioselectivities (up to 94 % ee ).
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