Preparation of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation and Hydrozincation of Ynamides

Benoit Gourdet; Mairi E. Rudkin; Ciorsdaidh A. Watts; Hon Wai Lam

doi:10.1021/jo901658v

Preparation of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation and Hydrozincation of Ynamides

Benoit Gourdet, Mairi E. Rudkin, Ciorsdaidh A. Watts, Hon Wai Lam

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

Abstract

Rhodium-catalyzed carbozincation of ynamides using diorganozinc reagents or functionalized organozinc halides is described. Using a tri(2-furyl)phosphine-modified rhodium catalyst, the reaction course is altered to hydrozincation when diethylzinc is employed as the organozinc reagent. Trapping of the alkenylzinc intermediates produced in these reactions in further functionalization reactions is possible. Collectively, these processes enable access to a range of multisubstituted enamides in stereo- and regiocontrolled fashion.

Original language	English
Pages (from-to)	7849-7858
Number of pages	10
Journal	The Journal of Organic Chemistry (JOC)
Volume	74
Issue number	20
DOIs	https://doi.org/10.1021/jo901658v
Publication status	Published - 16 Oct 2009

Keywords / Materials (for Non-textual outputs)

HIGHLY STEREOSELECTIVE-SYNTHESIS
RING-CLOSING METATHESIS
DIELS-ALDER REACTIONS
AZA-CLAISEN REARRANGEMENT
C-N
ORGANOZINC REAGENTS
COUPLING REACTIONS
ALKYNYL BROMIDES
TERMINAL ALKYNES
CHIRAL YNAMIDES

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10.1021/jo901658v

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title = "Preparation of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation and Hydrozincation of Ynamides",

abstract = "Rhodium-catalyzed carbozincation of ynamides using diorganozinc reagents or functionalized organozinc halides is described. Using a tri(2-furyl)phosphine-modified rhodium catalyst, the reaction course is altered to hydrozincation when diethylzinc is employed as the organozinc reagent. Trapping of the alkenylzinc intermediates produced in these reactions in further functionalization reactions is possible. Collectively, these processes enable access to a range of multisubstituted enamides in stereo- and regiocontrolled fashion.",

keywords = "HIGHLY STEREOSELECTIVE-SYNTHESIS, RING-CLOSING METATHESIS, DIELS-ALDER REACTIONS, AZA-CLAISEN REARRANGEMENT, C-N, ORGANOZINC REAGENTS, COUPLING REACTIONS, ALKYNYL BROMIDES, TERMINAL ALKYNES, CHIRAL YNAMIDES",

author = "Benoit Gourdet and Rudkin, {Mairi E.} and Watts, {Ciorsdaidh A.} and Lam, {Hon Wai}",

year = "2009",

month = oct,

day = "16",

doi = "10.1021/jo901658v",

language = "English",

volume = "74",

pages = "7849--7858",

journal = "The Journal of Organic Chemistry (JOC)",

issn = "1520-6904",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - Preparation of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation and Hydrozincation of Ynamides

AU - Gourdet, Benoit

AU - Rudkin, Mairi E.

AU - Watts, Ciorsdaidh A.

AU - Lam, Hon Wai

PY - 2009/10/16

Y1 - 2009/10/16

N2 - Rhodium-catalyzed carbozincation of ynamides using diorganozinc reagents or functionalized organozinc halides is described. Using a tri(2-furyl)phosphine-modified rhodium catalyst, the reaction course is altered to hydrozincation when diethylzinc is employed as the organozinc reagent. Trapping of the alkenylzinc intermediates produced in these reactions in further functionalization reactions is possible. Collectively, these processes enable access to a range of multisubstituted enamides in stereo- and regiocontrolled fashion.

AB - Rhodium-catalyzed carbozincation of ynamides using diorganozinc reagents or functionalized organozinc halides is described. Using a tri(2-furyl)phosphine-modified rhodium catalyst, the reaction course is altered to hydrozincation when diethylzinc is employed as the organozinc reagent. Trapping of the alkenylzinc intermediates produced in these reactions in further functionalization reactions is possible. Collectively, these processes enable access to a range of multisubstituted enamides in stereo- and regiocontrolled fashion.

KW - HIGHLY STEREOSELECTIVE-SYNTHESIS

KW - RING-CLOSING METATHESIS

KW - DIELS-ALDER REACTIONS

KW - AZA-CLAISEN REARRANGEMENT

KW - C-N

KW - ORGANOZINC REAGENTS

KW - COUPLING REACTIONS

KW - ALKYNYL BROMIDES

KW - TERMINAL ALKYNES

KW - CHIRAL YNAMIDES

UR - http://www.scopus.com/inward/record.url?scp=70349881440&partnerID=8YFLogxK

U2 - 10.1021/jo901658v

DO - 10.1021/jo901658v

M3 - Literature review

SN - 1520-6904

VL - 74

SP - 7849

EP - 7858

JO - The Journal of Organic Chemistry (JOC)

JF - The Journal of Organic Chemistry (JOC)

IS - 20

ER -

Preparation of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation and Hydrozincation of Ynamides

Abstract

Keywords / Materials (for Non-textual outputs)

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