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 language | English |
|---|---|
| Pages (from-to) | 5834-5841 |
| Number of pages | 8 |
| Journal | Journal of the American Chemical Society |
| Volume | 140 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2 May 2018 |
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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 journal › Article › Research › peer-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.
UR - http://www.scopus.com/inward/record.url?scp=85046421955&partnerID=8YFLogxK
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
IS - 17
ER -