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Organocatalytic Asymmetric Benzylation and Aldol‐Hemiacetalization of α,β‐Unsaturated Trifluoromethyl Ketones: Efficient Enantioselective Construction of 3,4‐Dihydroisocoumarins
Author(s) -
Duan Jindian,
Cheng Yuyu,
Cheng Jing,
Li Rou,
Li Pengfei
Publication year - 2017
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.201604920
Subject(s) - enantioselective synthesis , stereocenter , chemistry , trifluoromethyl , aldol reaction , organic chemistry , organocatalysis , optically active , tertiary amine , catalysis , stereochemistry , alkyl
A new method has been developed for the organocatalytic enantioselective benzylation and aldol‐hemiacetalization of α,β‐unsaturated trifluoromethyl ketones with toluene derivatives in the presence of a tertiary amine‐thiourea catalyst. This method represents a facile and efficient strategy for the asymmetric synthesis of optically active 3,4‐dihydroisocoumarins bearing a trifluoromethylated tetrasubstituted carbon stereocenter with high enantioselectivity. Notably, this strategy was used to synthesize several chiral trifluoromethylated analogues of typharin with high efficiency.