Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters

Alexander S. Dudnik, Todd Schwier, Vladimir Gevorgyan

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

A mild and stereoselective gold(I)-catalyzed domino transformation of propargylic esters leading to substituted (1E,3E)-dienes has been developed. This cascade process proceeds via a sequence of 1,3-acyloxy- or 1,3-phosphatyloxy migrations to form allenic intermediate followed by a proton transfer.

Original languageEnglish (US)
Pages (from-to)482-485
Number of pages4
JournalJournal of Organometallic Chemistry
Volume694
Issue number4
DOIs
StatePublished - Feb 15 2009
Externally publishedYes

Fingerprint

Proton transfer
dienes
Gold
Protons
esters
Esters
cascades
gold
protons
synthesis

Keywords

  • 1,3-Dienes
  • Gold
  • Homogeneous catalysis
  • Propargylic esters
  • Rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters. / Dudnik, Alexander S.; Schwier, Todd; Gevorgyan, Vladimir.

In: Journal of Organometallic Chemistry, Vol. 694, No. 4, 15.02.2009, p. 482-485.

Research output: Contribution to journalArticle

Dudnik, Alexander S. ; Schwier, Todd ; Gevorgyan, Vladimir. / Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters. In: Journal of Organometallic Chemistry. 2009 ; Vol. 694, No. 4. pp. 482-485.
@article{3a1501222266479db879903f99e15309,
title = "Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters",
abstract = "A mild and stereoselective gold(I)-catalyzed domino transformation of propargylic esters leading to substituted (1E,3E)-dienes has been developed. This cascade process proceeds via a sequence of 1,3-acyloxy- or 1,3-phosphatyloxy migrations to form allenic intermediate followed by a proton transfer.",
keywords = "1,3-Dienes, Gold, Homogeneous catalysis, Propargylic esters, Rearrangement",
author = "Dudnik, {Alexander S.} and Todd Schwier and Vladimir Gevorgyan",
year = "2009",
month = "2",
day = "15",
doi = "10.1016/j.jorganchem.2008.08.010",
language = "English (US)",
volume = "694",
pages = "482--485",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",
number = "4",

}

TY - JOUR

T1 - Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters

AU - Dudnik, Alexander S.

AU - Schwier, Todd

AU - Gevorgyan, Vladimir

PY - 2009/2/15

Y1 - 2009/2/15

N2 - A mild and stereoselective gold(I)-catalyzed domino transformation of propargylic esters leading to substituted (1E,3E)-dienes has been developed. This cascade process proceeds via a sequence of 1,3-acyloxy- or 1,3-phosphatyloxy migrations to form allenic intermediate followed by a proton transfer.

AB - A mild and stereoselective gold(I)-catalyzed domino transformation of propargylic esters leading to substituted (1E,3E)-dienes has been developed. This cascade process proceeds via a sequence of 1,3-acyloxy- or 1,3-phosphatyloxy migrations to form allenic intermediate followed by a proton transfer.

KW - 1,3-Dienes

KW - Gold

KW - Homogeneous catalysis

KW - Propargylic esters

KW - Rearrangement

UR - http://www.scopus.com/inward/record.url?scp=58649104163&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=58649104163&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2008.08.010

DO - 10.1016/j.jorganchem.2008.08.010

M3 - Article

C2 - 20161695

AN - SCOPUS:58649104163

VL - 694

SP - 482

EP - 485

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 4

ER -