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Bimetallic Gold(I)/Chiral N , N′ ‐Dioxide Nickel(II) Asymmetric Relay Catalysis: Chemo‐ and Enantioselective Synthesis of Spiroketals and Spiroaminals
Author(s) -
Li Jun,
Lin Lili,
Hu Bowen,
Lian Xiangjin,
Wang Gang,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201601701
Subject(s) - enantioselective synthesis , catalysis , bimetallic strip , chemistry , nickel , ligand (biochemistry) , yield (engineering) , combinatorial chemistry , lewis acids and bases , medicinal chemistry , organic chemistry , materials science , receptor , biochemistry , metallurgy
A highly efficient asymmetric cascade reaction between keto esters and alkynyl alcohols and amides is reported. The success of the reaction was attributed to the combination of chiral Lewis acid N , N′ ‐dioxide nickel(II) catalysis with achiral π‐acid gold(I) catalysis working as an asymmetric relay catalytic system. The corresponding spiroketals and spiroaminals were synthesized in up to 99 % yield, 19:1 d.r., and more than 99 % ee under mild reaction conditions. Control experiments suggest that the N , N′ ‐dioxide ligand was essential for the formation of the spiro products.
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