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Chiral Brønsted acid catalyzed enantioselective dehydrative Nazarov-type electrocyclization of aryl and 2‑thienyl vinyl alcohols
journal contribution
posted on 2023-05-19, 21:13 authored by Jin, J, Zhao, Y, Gouranourimi, A, Alireza AriafardAlireza Ariafard, Chan, PWHAn 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.
Funding
Australian Research Council
University of Wollongong
History
Publication title
Journal American Chemical SocietyVolume
140Issue
17Pagination
5834-5841ISSN
0002-7863Department/School
School of Natural SciencesPublisher
Amer Chemical SocPlace of publication
1155 16Th St, Nw, Washington, USA, Dc, 20036Rights statement
Copyright 2018 American Chemical SocietyRepository Status
- Restricted