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

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

Cite this

@article{a7baf0ca8bf44ca9b87312ac357d6750,
title = "Chiral Br{\o}nsted acid catalyzed enantioselective dehydrative nazarov-type electrocyclization of aryl and 2-thienyl vinyl alcohols",
abstract = "An efficient chiral Br{\o}nsted 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.",
author = "Jianwen Jin and Yichao Zhao and Ali Gouranourimi and Alireza Ariafard and Chan, {Philip Wai Hong}",
year = "2018",
month = "5",
day = "2",
doi = "10.1021/jacs.8b02339",
language = "English",
volume = "140",
pages = "5834--5841",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "ACS Publications",
number = "17",

}

Chiral Brønsted acid catalyzed enantioselective dehydrative nazarov-type electrocyclization of aryl and 2-thienyl vinyl alcohols. / Jin, Jianwen; Zhao, Yichao; Gouranourimi, Ali; Ariafard, Alireza; Chan, Philip Wai Hong.

In: Journal of the American Chemical Society, Vol. 140, No. 17, 02.05.2018, p. 5834-5841.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Chiral Brønsted acid catalyzed enantioselective dehydrative nazarov-type electrocyclization of aryl and 2-thienyl vinyl alcohols

AU - Jin, Jianwen

AU - Zhao, Yichao

AU - Gouranourimi, Ali

AU - Ariafard, Alireza

AU - Chan, Philip Wai Hong

PY - 2018/5/2

Y1 - 2018/5/2

N2 - 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.

AB - 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.

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U2 - 10.1021/jacs.8b02339

DO - 10.1021/jacs.8b02339

M3 - Article

VL - 140

SP - 5834

EP - 5841

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

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