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Organocatalytic Asymmetric Allylic Alkylation of Morita–Baylis–Hillman Carbonates with Phosphorus Ylides: Synthesis of Chiral 3‐Substituted 2,4‐Functionalized 1,4‐Pentadienes
Author(s) -
Lin Aijun,
Wang Junying,
Mao Haibin,
Shi Yan,
Mao Zhijie,
Zhu Chengjian
Publication year - 2013
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.201300738
Subject(s) - chemistry , tsuji–trost reaction , allylic rearrangement , catalysis , cinchona , organic chemistry , enantioselective synthesis , phosphorus , organocatalysis , alkylation , combinatorial chemistry , medicinal chemistry
A highly efficient asymmetric allylic substitution of Morita–Baylis–Hillman (MBH) carbonates with phosphorus ylides under the catalysis of modified cinchona alkaloids was developed. The reaction delivered products in moderate to good yields with excellent enantioselectivities (up to 98 % ee ) for a wide range of MBH carbonates. The scope of the reaction was demonstrated by the synthesis of chiral 3‐substituted 2,4‐functionalized 1,4‐pentadienes.