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Bifunctional Phase‐Transfer Catalysts Catalyzed Diastereo‐ and Enantioselective Aza‐Henry Reaction of β,γ‐Unsaturated Nitroalkenes With Amidosulfones
Author(s) -
Lu Ning,
Bai Fuquan,
Fang Yanhong,
Wei Zhonglin,
Cao Jungang,
Liang Dapeng,
Lin Yingjie,
Duan Haifeng
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700787
Subject(s) - bifunctional , enantioselective synthesis , chemistry , catalysis , cinchona , cinchona alkaloids , density functional theory , organocatalysis , combinatorial chemistry , organic chemistry , phase (matter) , computational chemistry
Abstract An efficient diastereo‐ and enantioselective aza‐Henry reaction of β,γ ‐unsaturated nitroalkenes with N‐ Boc amidosulfones has been realized under the catalysis of bifunctional chiral phase‐transfer catalysts bearing multiple H‐bonding donors, which was derived from cinchona alkaloids. This asymmetric catalytic protocol is suitable for a wide range of substrates, and give the corresponding products in high to excellent yields (up to 99%) with excellent diastereo‐ and enantioselectivities (up to >99 : 1 dr, up to >99% ee). Density functional theory (DFT) calculations are also performed and give the possible transition‐state model to illustrate the mechanism of the developed reaction.