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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, PWH
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.

Funding

Australian Research Council

University of Wollongong

History

Publication title

Journal American Chemical Society

Volume

140

Issue

17

Pagination

5834-5841

ISSN

0002-7863

Department/School

School of Natural Sciences

Publisher

Amer Chemical Soc

Place of publication

1155 16Th St, Nw, Washington, USA, Dc, 20036

Rights statement

Copyright 2018 American Chemical Society

Repository Status

  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences

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