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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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WRAP-Chiral-Bronsted-acid-catalyzed-enantioselective-Hong-Chan-2018.pdf - Accepted Version - Requires a PDF viewer. Download (950Kb) | Preview |
Official URL: http://doi.org/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 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 | ||||||||
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| 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: |
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| 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: |
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