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

Jianwen Jin, Yichao Zhao, Ali Gouranourimi, Alireza Ariafard, Philip Wai Hong Chan

Research output: Contribution to journalArticleResearchpeer-review

18 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5834-5841
Number of pages8
JournalJournal of the American Chemical Society
Volume140
Issue number17
DOIs
Publication statusPublished - 2 May 2018

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