Stereoselective Synthesis of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation of Ynamides

Benoit Gourdet; Hon Wai Lam

doi:10.1021/ja900946h

Stereoselective Synthesis of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation of Ynamides

Benoit Gourdet, Hon Wai Lam

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

Abstract

A new rhodium-catalyzed carbozincation of ynamides has been developed, using diorganozinc: reagents or functionatized alkylzinc: halides. The reactions are highly regio- and stereoselective, allowing access to a wide range of multisubstituted enamides, which are increasingly important building blocks for organic synthesis. Utilization of the alkenylzinc intermediates in further carbon-carbon bond-forming reactions to form trisubstituted enamides is also possible.

Original language	English
Pages (from-to)	3802-+
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	131
Issue number	11
DOIs	https://doi.org/10.1021/ja900946h
Publication status	Published - 25 Mar 2009

Keywords

COUPLING REACTIONS
CHIRAL ENAMIDES
TERMINAL ALKYNES
ALDEHYDES
CYCLOPROPANATION
NUCLEOPHILES
CHEMISTRY
REAGENTS
ETHERS

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10.1021/ja900946h

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title = "Stereoselective Synthesis of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation of Ynamides",

abstract = "A new rhodium-catalyzed carbozincation of ynamides has been developed, using diorganozinc: reagents or functionatized alkylzinc: halides. The reactions are highly regio- and stereoselective, allowing access to a wide range of multisubstituted enamides, which are increasingly important building blocks for organic synthesis. Utilization of the alkenylzinc intermediates in further carbon-carbon bond-forming reactions to form trisubstituted enamides is also possible.",

keywords = "COUPLING REACTIONS, CHIRAL ENAMIDES, TERMINAL ALKYNES, ALDEHYDES, CYCLOPROPANATION, NUCLEOPHILES, CHEMISTRY, REAGENTS, ETHERS",

author = "Benoit Gourdet and Lam, {Hon Wai}",

year = "2009",

month = mar,

day = "25",

doi = "10.1021/ja900946h",

language = "English",

volume = "131",

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journal = "Journal of the American Chemical Society",

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publisher = "American Chemical Society",

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T1 - Stereoselective Synthesis of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation of Ynamides

AU - Gourdet, Benoit

AU - Lam, Hon Wai

PY - 2009/3/25

Y1 - 2009/3/25

N2 - A new rhodium-catalyzed carbozincation of ynamides has been developed, using diorganozinc: reagents or functionatized alkylzinc: halides. The reactions are highly regio- and stereoselective, allowing access to a wide range of multisubstituted enamides, which are increasingly important building blocks for organic synthesis. Utilization of the alkenylzinc intermediates in further carbon-carbon bond-forming reactions to form trisubstituted enamides is also possible.

AB - A new rhodium-catalyzed carbozincation of ynamides has been developed, using diorganozinc: reagents or functionatized alkylzinc: halides. The reactions are highly regio- and stereoselective, allowing access to a wide range of multisubstituted enamides, which are increasingly important building blocks for organic synthesis. Utilization of the alkenylzinc intermediates in further carbon-carbon bond-forming reactions to form trisubstituted enamides is also possible.

KW - COUPLING REACTIONS

KW - CHIRAL ENAMIDES

KW - TERMINAL ALKYNES

KW - ALDEHYDES

KW - CYCLOPROPANATION

KW - NUCLEOPHILES

KW - CHEMISTRY

KW - REAGENTS

KW - ETHERS

UR - http://www.scopus.com/inward/record.url?scp=67749130975&partnerID=8YFLogxK

U2 - 10.1021/ja900946h

DO - 10.1021/ja900946h

M3 - Article

VL - 131

SP - 3802-+

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 11

ER -

Stereoselective Synthesis of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation of Ynamides

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Keywords

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