Au-Catalyzed Pentannulation Reaction of Propargylic Esters Occurring at C(sp3)-H Site

Kazem Roohollah Shiroodi, Masumi Sugawara, Maxim Ratushnyy, Douglas C. Yarbrough, Donald J. Wink, Vladimir Gevorgyan

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A gold-catalyzed cascade cyclization reaction of easily accessible propargylic esters to cyclopentenones has been developed. This transformation features an unprecedented pentannulation reaction of propargylic esters which occurs at an unactivated C(sp3)-H site to efficiently produce functionalized mono-, bis-, and tricyclic cyclopentenones.

Original languageEnglish (US)
Pages (from-to)4062-4065
Number of pages4
JournalOrganic Letters
Volume17
Issue number16
DOIs
StatePublished - Aug 7 2015
Externally publishedYes

Fingerprint

esters
Esters
Cyclization
Gold
cascades
gold
cyclopentenone

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Shiroodi, K. R., Sugawara, M., Ratushnyy, M., Yarbrough, D. C., Wink, D. J., & Gevorgyan, V. (2015). Au-Catalyzed Pentannulation Reaction of Propargylic Esters Occurring at C(sp3)-H Site. Organic Letters, 17(16), 4062-4065. https://doi.org/10.1021/acs.orglett.5b01983

Au-Catalyzed Pentannulation Reaction of Propargylic Esters Occurring at C(sp3)-H Site. / Shiroodi, Kazem Roohollah; Sugawara, Masumi; Ratushnyy, Maxim; Yarbrough, Douglas C.; Wink, Donald J.; Gevorgyan, Vladimir.

In: Organic Letters, Vol. 17, No. 16, 07.08.2015, p. 4062-4065.

Research output: Contribution to journalArticle

Shiroodi, KR, Sugawara, M, Ratushnyy, M, Yarbrough, DC, Wink, DJ & Gevorgyan, V 2015, 'Au-Catalyzed Pentannulation Reaction of Propargylic Esters Occurring at C(sp3)-H Site', Organic Letters, vol. 17, no. 16, pp. 4062-4065. https://doi.org/10.1021/acs.orglett.5b01983
Shiroodi, Kazem Roohollah ; Sugawara, Masumi ; Ratushnyy, Maxim ; Yarbrough, Douglas C. ; Wink, Donald J. ; Gevorgyan, Vladimir. / Au-Catalyzed Pentannulation Reaction of Propargylic Esters Occurring at C(sp3)-H Site. In: Organic Letters. 2015 ; Vol. 17, No. 16. pp. 4062-4065.
@article{0d5ca62990544be4b26e320c237d82e8,
title = "Au-Catalyzed Pentannulation Reaction of Propargylic Esters Occurring at C(sp3)-H Site",
abstract = "A gold-catalyzed cascade cyclization reaction of easily accessible propargylic esters to cyclopentenones has been developed. This transformation features an unprecedented pentannulation reaction of propargylic esters which occurs at an unactivated C(sp3)-H site to efficiently produce functionalized mono-, bis-, and tricyclic cyclopentenones.",
author = "Shiroodi, {Kazem Roohollah} and Masumi Sugawara and Maxim Ratushnyy and Yarbrough, {Douglas C.} and Wink, {Donald J.} and Vladimir Gevorgyan",
year = "2015",
month = "8",
day = "7",
doi = "10.1021/acs.orglett.5b01983",
language = "English (US)",
volume = "17",
pages = "4062--4065",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "16",

}

TY - JOUR

T1 - Au-Catalyzed Pentannulation Reaction of Propargylic Esters Occurring at C(sp3)-H Site

AU - Shiroodi, Kazem Roohollah

AU - Sugawara, Masumi

AU - Ratushnyy, Maxim

AU - Yarbrough, Douglas C.

AU - Wink, Donald J.

AU - Gevorgyan, Vladimir

PY - 2015/8/7

Y1 - 2015/8/7

N2 - A gold-catalyzed cascade cyclization reaction of easily accessible propargylic esters to cyclopentenones has been developed. This transformation features an unprecedented pentannulation reaction of propargylic esters which occurs at an unactivated C(sp3)-H site to efficiently produce functionalized mono-, bis-, and tricyclic cyclopentenones.

AB - A gold-catalyzed cascade cyclization reaction of easily accessible propargylic esters to cyclopentenones has been developed. This transformation features an unprecedented pentannulation reaction of propargylic esters which occurs at an unactivated C(sp3)-H site to efficiently produce functionalized mono-, bis-, and tricyclic cyclopentenones.

UR - http://www.scopus.com/inward/record.url?scp=84940204866&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84940204866&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b01983

DO - 10.1021/acs.orglett.5b01983

M3 - Article

C2 - 26246385

AN - SCOPUS:84940204866

VL - 17

SP - 4062

EP - 4065

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 16

ER -