Article ; Online: Design and Atroposelective Construction of IAN analogues by Organocatalytic Asymmetric Heteroannulation of Alkynes.
Angewandte Chemie (International ed. in English)
2020 Volume 59, Issue 51, Page(s) 23077–23082
Abstract: An organocatalytic atroposelective strategy for accessing enantioenriched axially chiral IAN ... tolerated a broad substrate scope, providing a facile organocatalytic approach to IAN analogues in good ... of this methodology was illustrated through further transformations into IAN-type ligand and axially chiral thiourea. ...
Abstract | 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. |
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Language | English |
Publishing date | 2020-10-15 |
Publishing country | Germany |
Document type | Journal Article ; Research Support, Non-U.S. Gov't |
ZDB-ID | 2011836-3 |
ISSN | 1521-3773 ; 1433-7851 |
ISSN (online) | 1521-3773 |
ISSN | 1433-7851 |
DOI | 10.1002/anie.202010598 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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