Enantioselective 1,4-additions of ClMeAl(CH=CHR) (R = alkyl, alkenyl, Ph) to cyclohexenones

Willcox, Darren; Woodward, Simon; Alexakis, Alexandre

doi:10.1039/c3cc48191c

Scientific article

English

Enantioselective 1,4-additions of ClMeAl(CH=CHR) (R = alkyl, alkenyl, Ph) to cyclohexenones

ContributorsWillcox, Darren; Woodward, Simon; Alexakis, Alexandre

Published inChemical communications, vol. 50, no. 14, p. 1655-1657

Publication date2014

Abstract

Chloromethylvinyl alanes (E)-ClMeAl(CH[double bond, length as m-dash]CHR) prepared directly from terminal alkynes undergo 1,4-addition to cyclohexenone and 3-methylcyclohexenone in moderate to good yield (30–70%) and good to excellent stereoselectivity (80–98% ee) using readily available copper(I) sources and chiral ligands.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

WILLCOX, Darren, WOODWARD, Simon, ALEXAKIS, Alexandre. Enantioselective 1,4-additions of ClMeAl(CH=CHR) (R = alkyl, alkenyl, Ph) to cyclohexenones. In: Chemical communications, 2014, vol. 50, n° 14, p. 1655–1657. doi: 10.1039/c3cc48191c

Article (Published version)

Identifiers

PID : unige:33671
DOI : 10.1039/c3cc48191c

Commercial URLhttp://xlink.rsc.org/?DOI=c3cc48191c

Journal ISSN1359-7345

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Creation23/01/2014 16:29:00

First validation23/01/2014 16:29:00

Update time14/03/2023 20:53:50

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Enantioselective 1,4-additions of ClMeAl(CH=CHR) (R = alkyl, alkenyl, Ph) to cyclohexenones

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