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

Alexander S. Dudnik; Todd Schwier; Vladimir Gevorgyan

doi:10.1016/j.jorganchem.2008.08.010

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

Alexander S. Dudnik, Todd Schwier, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

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 language	English (US)
Pages (from-to)	482-485
Number of pages	4
Journal	Journal of Organometallic Chemistry
Volume	694
Issue number	4
DOIs	https://doi.org/10.1016/j.jorganchem.2008.08.010
State	Published - Feb 15 2009
Externally published	Yes

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

Access to Document

10.1016/j.jorganchem.2008.08.010

Cite this

@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",

note = "Funding Information: The support of the National Institutes of Health (Grant GM-64444) is gratefully acknowledged. ",

year = "2009",

month = feb,

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

N1 - Funding Information: The support of the National Institutes of Health (Grant GM-64444) is gratefully acknowledged.

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

SN - 0022-328X

VL - 694

SP - 482

EP - 485

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 4

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this