N-Heterocyclic Carbene-Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes

Carmen Concellon; Nicolas Duguet; Andrew D. Smith

doi:10.1002/adsc.200900538

N-Heterocyclic Carbene-Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes

Carmen Concellon, Nicolas Duguet, Andrew D. Smith

Research output: Contribution to journal › Review article › peer-review

Abstract

Chiral N-heterocyclic carbenes (NHCs) mediate the enantioselective addition of 2-phenylphenol to unsymmetrical alkylarylketenes, delivering alpha-alkyl-alpha-arylacetic acid derivatives with good levels of enantiocontrol (up to 84% ee). Enantiodivergent stereochemical outcomes are observed using 2-phenylphenol and benzhydrol in the NHC-promoted esterification reaction using a triazolium precatalyst derived from pyroglutamic acid, consistent with distinct mechanistic pathways operating within these processes.

Original language	English
Pages (from-to)	3001-3009
Number of pages	9
Journal	Advanced Synthesis & Catalysis
Volume	351
Issue number	17
DOIs	https://doi.org/10.1002/adsc.200900538
Publication status	Published - Nov 2009

Keywords

asymmetric catalysis
enantioselectivity
esters
ketenes
N-heterocyclic carbenes
organocatalysis
INTERMOLECULAR STETTER REACTION
DIELS-ALDER REACTIONS
METHYL ALPHA-PHENYLPROPIONATE
RING-OPENING POLYMERIZATION
SYNTHESEN MIT KETENEN
LOW CATALYST LOADINGS
C-CARBOXYL TRANSFER
ASYMMETRIC-SYNTHESIS
ALPHA,BETA-UNSATURATED ALDEHYDES
LIVING POLYMERIZATION

Access to Document

10.1002/adsc.200900538

Cite this

@article{fa0bf66e19fb4e8d9387965a8003c33b,

title = "N-Heterocyclic Carbene-Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes",

abstract = "Chiral N-heterocyclic carbenes (NHCs) mediate the enantioselective addition of 2-phenylphenol to unsymmetrical alkylarylketenes, delivering alpha-alkyl-alpha-arylacetic acid derivatives with good levels of enantiocontrol (up to 84\% ee). Enantiodivergent stereochemical outcomes are observed using 2-phenylphenol and benzhydrol in the NHC-promoted esterification reaction using a triazolium precatalyst derived from pyroglutamic acid, consistent with distinct mechanistic pathways operating within these processes.",

keywords = "asymmetric catalysis, enantioselectivity, esters, ketenes, N-heterocyclic carbenes, organocatalysis, INTERMOLECULAR STETTER REACTION, DIELS-ALDER REACTIONS, METHYL ALPHA-PHENYLPROPIONATE, RING-OPENING POLYMERIZATION, SYNTHESEN MIT KETENEN, LOW CATALYST LOADINGS, C-CARBOXYL TRANSFER, ASYMMETRIC-SYNTHESIS, ALPHA,BETA-UNSATURATED ALDEHYDES, LIVING POLYMERIZATION",

author = "Carmen Concellon and Nicolas Duguet and Smith, \{Andrew D.\}",

year = "2009",

month = nov,

doi = "10.1002/adsc.200900538",

language = "English",

volume = "351",

pages = "3001--3009",

journal = "Advanced Synthesis \& Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH, Weinheim",

number = "17",

}

TY - JOUR

T1 - N-Heterocyclic Carbene-Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes

AU - Concellon, Carmen

AU - Duguet, Nicolas

AU - Smith, Andrew D.

PY - 2009/11

Y1 - 2009/11

N2 - Chiral N-heterocyclic carbenes (NHCs) mediate the enantioselective addition of 2-phenylphenol to unsymmetrical alkylarylketenes, delivering alpha-alkyl-alpha-arylacetic acid derivatives with good levels of enantiocontrol (up to 84% ee). Enantiodivergent stereochemical outcomes are observed using 2-phenylphenol and benzhydrol in the NHC-promoted esterification reaction using a triazolium precatalyst derived from pyroglutamic acid, consistent with distinct mechanistic pathways operating within these processes.

AB - Chiral N-heterocyclic carbenes (NHCs) mediate the enantioselective addition of 2-phenylphenol to unsymmetrical alkylarylketenes, delivering alpha-alkyl-alpha-arylacetic acid derivatives with good levels of enantiocontrol (up to 84% ee). Enantiodivergent stereochemical outcomes are observed using 2-phenylphenol and benzhydrol in the NHC-promoted esterification reaction using a triazolium precatalyst derived from pyroglutamic acid, consistent with distinct mechanistic pathways operating within these processes.

KW - asymmetric catalysis

KW - enantioselectivity

KW - esters

KW - ketenes

KW - N-heterocyclic carbenes

KW - organocatalysis

KW - INTERMOLECULAR STETTER REACTION

KW - DIELS-ALDER REACTIONS

KW - METHYL ALPHA-PHENYLPROPIONATE

KW - RING-OPENING POLYMERIZATION

KW - SYNTHESEN MIT KETENEN

KW - LOW CATALYST LOADINGS

KW - C-CARBOXYL TRANSFER

KW - ASYMMETRIC-SYNTHESIS

KW - ALPHA,BETA-UNSATURATED ALDEHYDES

KW - LIVING POLYMERIZATION

UR - https://www.scopus.com/pages/publications/72149094300

U2 - 10.1002/adsc.200900538

DO - 10.1002/adsc.200900538

M3 - Review article

SN - 1615-4150

VL - 351

SP - 3001

EP - 3009

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

IS - 17

ER -

N-Heterocyclic Carbene-Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

N-Heterocyclic Carbenes as Asymmetric: N-Heterocyclic Carbenes as Asymmetric Organocatalysts: Reaction Development

Cite this

N-Heterocyclic Carbene-Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Projects

N-Heterocyclic Carbenes as Asymmetric: N-Heterocyclic Carbenes as Asymmetric Organocatalysts: Reaction Development

Cite this