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N , N′ ‐Dioxide–Lanthanum(III)‐Catalyzed Asymmetric Cyclopropanation of 2‐Cyano‐3‐arylacrylates with 2‐Bromomalonates
Author(s) -
Zhang Yuheng,
Lin Lili,
Chen Yushuang,
Liu Xiaohua,
Feng Xiaoming
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.201700212
Subject(s) - chemistry , cyclopropanation , enantioselective synthesis , halogenation , catalysis , stereoselectivity , lanthanum , medicinal chemistry , tandem , ring (chemistry) , combinatorial chemistry , organic chemistry , materials science , composite material
An efficient N , N′ ‐dioxide–lanthanum(III) complex catalytic system has been developed for the diastereo‐ and enantioselective Michael‐initiated ring‐closure (MIRC) reaction of 2‐cyano‐3‐arylacrylates with 2‐bromomalonates. Various chiral cyclopropanes with multiple substitutions were obtained in high yields (up to 93%) with excellent dr (>95:5 dr ) and good ee values (up to 91% ee ). The catalytic system also worked for the tandem halogenation/asymmetric MIRC reaction of α,β‐unsaturated nitriles, malonates and NBS. Besides, a possible catalytic model has been proposed to explain the origin of the stereoselectivity.