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A Brønsted Acid‐Catalyzed Michael Addition/Cyclization Sequence for the Diastereoselective Assembly of Chroman‐Bridged Polycyclic Isoindolinones
Author(s) -
Jin Shaojing,
Guo Jia,
Fang Dongmei,
Huang Yongwei,
Wang Qilin,
Bu Zhanwei
Publication year - 2019
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.201801227
Subject(s) - chemistry , michael reaction , catalysis , carboxylate , combinatorial chemistry , sequence (biology) , brønsted–lowry acid–base theory , organocatalysis , stereochemistry , organic chemistry , enantioselective synthesis , biochemistry
The first p ‐TSA‐catalyzed highly diastereoselective Michael addition/cyclization of 3‐carboxylate‐substituted isoindolinones and ortho ‐hydroxychalcones was developed to access a wide range of chroman‐bridged polycyclic isoindolinones. This reaction represents a novel and efficient method for the construction of complex bridged polycyclic isoindolinones. Moreover, several derivatizations were carried out to further highlight the synthetic value of this protocol.