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Chiral Brønsted acid catalyzed enantioselective dehydrative Nazarov-type electrocyclization of aryl and 2‑thienyl vinyl alcohols

Citation

Jin, J and Zhao, Y and Gouranourimi, A and Ariafard, A and Chan, PWH, Chiral Brønsted acid catalyzed enantioselective dehydrative Nazarov-type electrocyclization of aryl and 2‑thienyl vinyl alcohols, Journal American Chemical Society, 140, (17) pp. 5834-5841. ISSN 0002-7863 (2018) [Refereed Article]

Copyright Statement

Copyright 2018 American Chemical Society

DOI: doi:10.1021/jacs.8b02339

Abstract

An efficient chiral Brønsted acid-catalyzed enantioselective dehydrative Nazarov-type electrocyclization (DNE) of electron-rich aryl- and 2-thienyl-β-amino-2-en-1-ols is described. The 4π conrotatory electrocyclization reaction affords access to a wide variety of the corresponding 1H-indenes and 4H-cyclopenta[b]thiophenes in excellent yields of up to 99% and enantiomeric excess (ee) values of up to 99%. Experimental and computational studies based on a proposed intimate contact ionpair species that is further assisted by hydrogen bonding between the amino group of the substrate cation and chiral catalyst anion provide insight into the observed product enantioselectivities.

Item Details

Item Type:Refereed Article
Keywords:Nazarov, Computational Chemistry, DFT
Research Division:Chemical Sciences
Research Group:Inorganic Chemistry
Research Field:Transition Metal Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Gouranourimi, A (Mr Ali gouranourimi)
Author:Ariafard, A (Associate Professor Alireza Ariafard)
ID Code:128292
Year Published:2018
Funding Support:Australian Research Council (DP180100904)
Web of Science® Times Cited:1
Deposited By:Chemistry
Deposited On:2018-09-12
Last Modified:2018-10-04
Downloads:0

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