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Design and Atroposelective Construction of IAN analogues by Organocatalytic Asymmetric Heteroannulation of Alkynes
Author(s) -
Zhang Lei,
Shen Jiahua,
Wu San,
Zhong Guofu,
Wang YongBin,
Tan Bin
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202010598
Subject(s) - chemistry , combinatorial chemistry , thiourea , phosphoric acid , catalysis , substrate (aquarium) , scope (computer science) , organocatalysis , organic chemistry , enantioselective synthesis , computer science , oceanography , programming language , geology
An organocatalytic atroposelective strategy for accessing enantioenriched axially chiral IAN analogues was developed for the first time. A class of novel atropisomeric C2‐arylquinoline skeletons were synthesized with high enantiocontrol via chiral phosphoric‐acid‐catalyzed heteroannulation of in situ generated vinylidene ortho ‐quinone methide (VQM) intermediates with ortho ‐aminophenones. The strategy tolerated a broad substrate scope, providing a facile organocatalytic approach to IAN analogues in good yields and excellent enantioselectivities under mild reaction conditions. Moreover, the synthetic utility of this methodology was illustrated through further transformations into IAN‐type ligand and axially chiral thiourea.