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Phosphine Catalyzed Enantioselective Cascade Reaction Initiated by Intermolecular Cross Rauhut‐Currier Reaction of Electron‐Deficient ortho ‐Formyl Styrenes
Author(s) -
Liang ShuYuan,
Jiang Bo,
Xiao BenXian,
Chen ZhiChao,
Du. Wei,
Chen YingChun
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202000910
Subject(s) - enantioselective synthesis , annulation , chemistry , intermolecular force , catalysis , phosphine , aldol reaction , cascade reaction , organocatalysis , medicinal chemistry , stereochemistry , organic chemistry , molecule
The Rauhut‐Currier reaction generally employs α,β‐unsaturated carbonyl compounds and nitroalkenes as the substrates. Here we develop an enantioselective formal [4+2] annulation reaction, which is initiated by an intermolecular cross Rauhut‐Currier reaction between electron‐deficient ortho ‐formyl‐styrenes and 2‐benzoyl‐acrylonitriles catalyzed by an L ‐phenylglycine‐derived phosphine, followed by a cascade aldol/acyl transfer/elimination process. A series of enantioenriched dialin frameworks with an unusual exo ‐double bond are furnished in fair to good yields with moderate to excellent enantioselectivity, and the architectures with higher molecular complexity can be constructed via simple transformations.