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

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10.1039/c0cc03669b

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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",

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doi = "10.1039/c0cc03669b",

language = "English (US)",

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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.

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UR - https://www.scopus.com/pages/publications/78649660544#tab=citedBy

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DO - 10.1039/c0cc03669b

M3 - Article

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AN - SCOPUS:78649660544

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JO - Chemical Communications

JF - Chemical Communications

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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

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