NHC-Mediated Chlorination of Unsymmetrical Ketenes: Catalysis and Asymmetry

James Douglas; Kenneth B. Ling; Carmen Concellon; Gwydion Churchill; Alexandra M. Z. Slawin; Andrew D. Smith

doi:10.1002/ejoc.201000864

NHC-Mediated Chlorination of Unsymmetrical Ketenes: Catalysis and Asymmetry

James Douglas, Kenneth B. Ling, Carmen Concellon, Gwydion Churchill, Alexandra M. Z. Slawin, Andrew D. Smith

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

Abstract

NHCs promote the efficient chlorination of unsymmetrical disubstituted ketenes with a range of chlorinating agents; chiral NHCs display promising levels of asymmetric induction in the chlorination process with up to 61 % ee observed using 2,3,4,5,6,6-hexachlorocyclohexa-2,4-dienone.

Original language	English
Pages (from-to)	5863-5869
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	30
DOIs	https://doi.org/10.1002/ejoc.201000864
Publication status	Published - Oct 2010

Keywords

Homogeneous catalysis
Asymmetric synthesis
N-Heterocyclic carbene
Ketenes
Chlorination
N-HETEROCYCLIC CARBENE
HIGHLY ENANTIOSELECTIVE SYNTHESIS
C-CARBOXYL TRANSFER
BETA-KETO-ESTERS
ALPHA-CHLORINATION
KINETIC RESOLUTION
CARBONYL-COMPOUNDS
ACID-CHLORIDES
QUATERNARY STEREOCENTERS
1,3-DICARBONYL COMPOUNDS

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@article{37e828d7e1cf44f2a2597b0c0bd43772,

title = "NHC-Mediated Chlorination of Unsymmetrical Ketenes: Catalysis and Asymmetry",

abstract = "NHCs promote the efficient chlorination of unsymmetrical disubstituted ketenes with a range of chlorinating agents; chiral NHCs display promising levels of asymmetric induction in the chlorination process with up to 61 % ee observed using 2,3,4,5,6,6-hexachlorocyclohexa-2,4-dienone.",

keywords = "Homogeneous catalysis, Asymmetric synthesis, N-Heterocyclic carbene, Ketenes, Chlorination, N-HETEROCYCLIC CARBENE, HIGHLY ENANTIOSELECTIVE SYNTHESIS, C-CARBOXYL TRANSFER, BETA-KETO-ESTERS, ALPHA-CHLORINATION, KINETIC RESOLUTION, CARBONYL-COMPOUNDS, ACID-CHLORIDES, QUATERNARY STEREOCENTERS, 1,3-DICARBONYL COMPOUNDS",

author = "James Douglas and Ling, {Kenneth B.} and Carmen Concellon and Gwydion Churchill and Slawin, {Alexandra M. Z.} and Smith, {Andrew D.}",

year = "2010",

month = oct,

doi = "10.1002/ejoc.201000864",

language = "English",

pages = "5863--5869",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

number = "30",

}

TY - JOUR

T1 - NHC-Mediated Chlorination of Unsymmetrical Ketenes: Catalysis and Asymmetry

AU - Douglas, James

AU - Ling, Kenneth B.

AU - Concellon, Carmen

AU - Churchill, Gwydion

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

PY - 2010/10

Y1 - 2010/10

N2 - NHCs promote the efficient chlorination of unsymmetrical disubstituted ketenes with a range of chlorinating agents; chiral NHCs display promising levels of asymmetric induction in the chlorination process with up to 61 % ee observed using 2,3,4,5,6,6-hexachlorocyclohexa-2,4-dienone.

AB - NHCs promote the efficient chlorination of unsymmetrical disubstituted ketenes with a range of chlorinating agents; chiral NHCs display promising levels of asymmetric induction in the chlorination process with up to 61 % ee observed using 2,3,4,5,6,6-hexachlorocyclohexa-2,4-dienone.

KW - Homogeneous catalysis

KW - Asymmetric synthesis

KW - N-Heterocyclic carbene

KW - Ketenes

KW - Chlorination

KW - N-HETEROCYCLIC CARBENE

KW - HIGHLY ENANTIOSELECTIVE SYNTHESIS

KW - C-CARBOXYL TRANSFER

KW - BETA-KETO-ESTERS

KW - ALPHA-CHLORINATION

KW - KINETIC RESOLUTION

KW - CARBONYL-COMPOUNDS

KW - ACID-CHLORIDES

KW - QUATERNARY STEREOCENTERS

KW - 1,3-DICARBONYL COMPOUNDS

U2 - 10.1002/ejoc.201000864

DO - 10.1002/ejoc.201000864

M3 - Article

SN - 1434-193X

SP - 5863

EP - 5869

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 30

ER -

NHC-Mediated Chlorination of Unsymmetrical Ketenes: Catalysis and Asymmetry

Abstract

Keywords

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