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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201801824
Subject(s) - cycloaddition , intramolecular force , enantioselective synthesis , chemistry , combinatorial chemistry , axial chirality , aryl , organocatalysis , catalysis , stereochemistry , organic chemistry , alkyl
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.