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Catalytic Enantioselective [2+2] Cycloaddition of α‐Halo Acroleins: Construction of Cyclobutanes Containing Two Tetrasubstituted Stereocenters
Author(s) -
Zeng Lei,
Xu Jingjing,
Zhang Dongsheng,
Yan Zhongliang,
Cheng Guolin,
Rao Weidong,
Gao Lizhu
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202008465
Subject(s) - stereocenter , enantioselective synthesis , cyclobutanes , cycloaddition , catalysis , chemistry , vicinal , stereochemistry , stereoselectivity , combinatorial chemistry , organic chemistry
A catalytic enantioselective formal [2+2] cycloaddition between α‐halo acroleins and electronically diverse arylalkenes is described. In the presence of (S)‐oxazaborolidinium cation as the catalyst, densely functionalized cyclobutanes containing two vicinal tetrasubstituted stereocenters were produced in high yields and high diastereoselectivities with excellent enantioselectivities. Mechanistic studies revealed that the cis isomer could be transformed into the trans isomer via an enantiocontrolled process. A gram‐scale reaction of this catalytic method was used to demonstrate its synthetic potential.