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

Jin, J, Zhao, Y, Gouranourimi, A ORCID: 0000-0003-3354-5958, Ariafard, A ORCID: 0000-0003-2383-6380 and Chan, PWH 2018 , 'Chiral Brønsted acid catalyzed enantioselective dehydrative Nazarov-type electrocyclization of aryl and 2‑thienyl vinyl alcohols' , Journal American Chemical Society, vol. 140, no. 17 , pp. 5834-5841 , doi: 10.1021/jacs.8b02339.

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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 Type: Article
Authors/Creators:Jin, J and Zhao, Y and Gouranourimi, A and Ariafard, A and Chan, PWH
Keywords: Nazarov, Computational Chemistry, DFT
Journal or Publication Title: Journal American Chemical Society
Publisher: Amer Chemical Soc
ISSN: 0002-7863
DOI / ID Number: 10.1021/jacs.8b02339
Copyright Information:

Copyright 2018 American Chemical Society

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