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

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Jin, Jianwen, Zhao, Yichao, Gouranourimi, Ali, Ariafard, Alireza and Chan, Philip Wai Hong (2018) Chiral Brønsted acid catalyzed enantioselective dehydrative Nazarov-type electrocyclization of aryl and 2-Thienyl vinyl alcohols. Journal of the American Chemical Society, 140 (17). pp. 5834-5841. doi:10.1021/jacs.8b02339

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Official URL: http://doi.org/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 ion-pair 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: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Chemistry
SWORD Depositor: Library Publications Router
Library of Congress Subject Headings (LCSH): Enantioselective catalysis
Journal or Publication Title: Journal of the American Chemical Society
Publisher: American Chemical Society
ISSN: 1520-5126
Official Date: 2 May 2018
Dates:
DateEvent
2 May 2018Published
9 April 2018Available
9 April 2018Accepted
Date of first compliant deposit: 30 May 2018
Volume: 140
Number: 17
Page Range: pp. 5834-5841
DOI: 10.1021/jacs.8b02339
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
UNSPECIFIED[ARC] Australian Research Councilhttp://dx.doi.org/10.13039/501100000923

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