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Lewis Base Assisted Brønsted Base Catalysis: Direct Asymmetric Allylic Alkylation of Indenes
Author(s) -
Cui HaiLei,
Sun XunHao,
Jiang Lin,
Dong Lin,
Chen YingChun
Publication year - 2011
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.201101255
Subject(s) - chemistry , tsuji–trost reaction , cinchona , lewis acids and bases , catalysis , alkylation , base (topology) , allylic rearrangement , enantioselective synthesis , anthraquinone , organic chemistry , organocatalysis , stereochemistry , combinatorial chemistry , medicinal chemistry , mathematical analysis , mathematics
A direct, asymmetric allylic alkylation of indenes withMorita–Baylis–Hillman (MBH) carbonates has been developed based on a Lewis base assisted Brønsted base catalysis strategy. This process is promoted by a modified cinchona alkaloid hydroquinidine (anthraquinone‐1,4‐diyl) diether [(DHQD) 2 AQN] and gives rise to multifunctional chiral indene derivatives with moderate to excellent enantioselectivities (53–95 % ee ), albeit in low to modest yields (27–71 %).
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