The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: An efficient synthesis of (1Z, 3E)-1-bromo/chloro-2- carboxy-1,3-dienes

Yanzhao Wang; Biao Lu; Liming Zhang

doi:10.1039/c0cc03669b

The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: An efficient synthesis of (1Z, 3E)-1-bromo/chloro-2- carboxy-1,3-dienes

Yanzhao Wang, Biao Lu, Liming Zhang

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

49 Scopus citations

Abstract

A gold-catalyzed synthesis of 1-bromo/chloro-2-carboxy-1,3-dienes is developed using propargylic carboxylates containing halogenated alkynes as substrates. The reaction is highly diastereoselective, and the halogen atom at the alkyne terminus selectively promotes a 1,2-acyloxy migration. The diene products participate in the Diels-Alder and cross-coupling reactions.

Original language	English (US)
Pages (from-to)	9179-9181
Number of pages	3
Journal	Chemical Communications
Volume	46
Issue number	48
DOIs	https://doi.org/10.1039/c0cc03669b
State	Published - Dec 28 2010
Externally published	Yes

Publisher link

10.1039/c0cc03669b

Find It

Find It at U of M Libraries

Cite this

@article{67712c245d3442ec8123447cf000ff1d,

title = "The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: An efficient synthesis of (1Z, 3E)-1-bromo/chloro-2- carboxy-1,3-dienes",

abstract = "A gold-catalyzed synthesis of 1-bromo/chloro-2-carboxy-1,3-dienes is developed using propargylic carboxylates containing halogenated alkynes as substrates. The reaction is highly diastereoselective, and the halogen atom at the alkyne terminus selectively promotes a 1,2-acyloxy migration. The diene products participate in the Diels-Alder and cross-coupling reactions.",

author = "Yanzhao Wang and Biao Lu and Liming Zhang",

year = "2010",

month = dec,

day = "28",

doi = "10.1039/c0cc03669b",

language = "English (US)",

volume = "46",

pages = "9179--9181",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "48",

}

TY - JOUR

T1 - The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates

T2 - An efficient synthesis of (1Z, 3E)-1-bromo/chloro-2- carboxy-1,3-dienes

AU - Wang, Yanzhao

AU - Lu, Biao

AU - Zhang, Liming

PY - 2010/12/28

Y1 - 2010/12/28

N2 - A gold-catalyzed synthesis of 1-bromo/chloro-2-carboxy-1,3-dienes is developed using propargylic carboxylates containing halogenated alkynes as substrates. The reaction is highly diastereoselective, and the halogen atom at the alkyne terminus selectively promotes a 1,2-acyloxy migration. The diene products participate in the Diels-Alder and cross-coupling reactions.

AB - A gold-catalyzed synthesis of 1-bromo/chloro-2-carboxy-1,3-dienes is developed using propargylic carboxylates containing halogenated alkynes as substrates. The reaction is highly diastereoselective, and the halogen atom at the alkyne terminus selectively promotes a 1,2-acyloxy migration. The diene products participate in the Diels-Alder and cross-coupling reactions.

UR - http://www.scopus.com/inward/record.url?scp=78649660544&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=78649660544&partnerID=8YFLogxK

U2 - 10.1039/c0cc03669b

DO - 10.1039/c0cc03669b

M3 - Article

C2 - 21038044

AN - SCOPUS:78649660544

SN - 1359-7345

VL - 46

SP - 9179

EP - 9181

JO - Chemical Communications

JF - Chemical Communications

IS - 48

ER -

The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: An efficient synthesis of (1Z, 3E)-1-bromo/chloro-2- carboxy-1,3-dienes

Abstract

Publisher link

Find It

Other files and links

Fingerprint

Cite this