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A Strategy Enabling Enantioselective Direct Conjugate Addition of Inert Aryl Methane Nucleophiles to Enals with a Chiral Amine Catalyst under Mild Conditions
Author(s) -
Li Tengfei,
Zhu Jin,
Wu Deyan,
Li Xiangmin,
Wang Sinan,
Li Hao,
Li Jian,
Wang Wei
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300304
Subject(s) - nucleophile , enantioselective synthesis , conjugate , nitro , aryl , chemistry , catalysis , amine gas treating , combinatorial chemistry , organic chemistry , mathematics , mathematical analysis , alkyl
Nitro‐charged activation : An organocatalytic enantioselective conjugate addition of aryl methyl nucleophiles to enals has been developed to produce ubiquitous chiral benzylic building blocks (see scheme; TES=triethylsilyl). Taking advantage of the strongly electron‐withdrawing nature of nitro groups, which can be conveniently transformed into other functionalities, this functionality was incorporated into aromatic systems as a temporary activating group.