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Organocatalytic Atroposelective Intramolecular [4+2] Cycloaddition: Synthesis of Axially Chiral Heterobiaryls
Author(s) -
Liu Yidong,
Wu Xiaoyan,
Li Shan,
Xue Lu,
Shan Chunhui,
Zhao Zhengxing,
Yan Hailong
Publication year - 2018
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.201801824
Subject(s) - intramolecular force , cycloaddition , enantioselective synthesis , chemistry , axial symmetry , combinatorial chemistry , aryl , catalysis , stereochemistry , computational chemistry , organic chemistry , mathematics , alkyl , geometry
The enantioselective construction of axially chiral aryl‐naphthopyran skeletons was realized by organocatalytic atroposelective intramolecular [4+2] cycloaddition of in situ generated vinylidene ortho ‐quinone methides, from 2‐ethynylphenol derivatives, with alkynes. Through this method, the heteroatropisomers were obtained with excellent yields and enantioselectivities. Moreover, a speculative model of the stereochemical outcome is proposed based on preliminary mechanistic studies. The products having various functional groups can be easily transformed into valuable intermediates as either potential ligands or organocatalysts.