alpha-Aroyloxyaldehydes: scope and limitations as alternatives to alpha-haloaldehydes for NHC-catalysed redox transformations

Kenneth B. Ling; Andrew D. Smith

doi:10.1039/c0cc02456b

alpha-Aroyloxyaldehydes: scope and limitations as alternatives to alpha-haloaldehydes for NHC-catalysed redox transformations

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

Abstract

alpha-Aroyloxyaldehydes are readily prepared bench stable synthetic intermediates. Their ability to act as alpha-haloaldehyde surrogates for NHC-promoted redox esterifications and in [4+2] cycloadditions is described.

Original language	English
Pages (from-to)	373-375
Number of pages	3
Journal	Chemical Communications
Volume	47
Issue number	1
DOIs	https://doi.org/10.1039/c0cc02456b
Publication status	Published - 2011

Keywords

N-HETEROCYCLIC CARBENES
DIELS-ALDER REACTIONS
RING EXPANSION
ALPHA,BETA-UNSATURATED ALDEHYDES
STEREOSELECTIVE-SYNTHESIS
ACTIVATED CARBOXYLATES
NUCLEOPHILIC CARBENES
ESTERS
OXIDATION
GENERATION

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10.1039/c0cc02456b

N-Heterocyclic Carbenes as Asymmetric: N-Heterocyclic Carbenes as Asymmetric Organocatalysts: Reaction Development
Smith, A. D. (PI)
EPSRC
1/04/07 → 30/09/10
Project: Standard

Cite this

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title = "alpha-Aroyloxyaldehydes: scope and limitations as alternatives to alpha-haloaldehydes for NHC-catalysed redox transformations",

abstract = "alpha-Aroyloxyaldehydes are readily prepared bench stable synthetic intermediates. Their ability to act as alpha-haloaldehyde surrogates for NHC-promoted redox esterifications and in [4+2] cycloadditions is described.",

keywords = "N-HETEROCYCLIC CARBENES, DIELS-ALDER REACTIONS, RING EXPANSION, ALPHA,BETA-UNSATURATED ALDEHYDES, STEREOSELECTIVE-SYNTHESIS, ACTIVATED CARBOXYLATES, NUCLEOPHILIC CARBENES, ESTERS, OXIDATION, GENERATION",

author = "Ling, {Kenneth B.} and Smith, {Andrew D.}",

year = "2011",

doi = "10.1039/c0cc02456b",

language = "English",

volume = "47",

pages = "373--375",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "1",

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TY - JOUR

T1 - alpha-Aroyloxyaldehydes: scope and limitations as alternatives to alpha-haloaldehydes for NHC-catalysed redox transformations

AU - Ling, Kenneth B.

AU - Smith, Andrew D.

PY - 2011

Y1 - 2011

N2 - alpha-Aroyloxyaldehydes are readily prepared bench stable synthetic intermediates. Their ability to act as alpha-haloaldehyde surrogates for NHC-promoted redox esterifications and in [4+2] cycloadditions is described.

AB - alpha-Aroyloxyaldehydes are readily prepared bench stable synthetic intermediates. Their ability to act as alpha-haloaldehyde surrogates for NHC-promoted redox esterifications and in [4+2] cycloadditions is described.

KW - N-HETEROCYCLIC CARBENES

KW - DIELS-ALDER REACTIONS

KW - RING EXPANSION

KW - ALPHA,BETA-UNSATURATED ALDEHYDES

KW - STEREOSELECTIVE-SYNTHESIS

KW - ACTIVATED CARBOXYLATES

KW - NUCLEOPHILIC CARBENES

KW - ESTERS

KW - OXIDATION

KW - GENERATION

U2 - 10.1039/c0cc02456b

DO - 10.1039/c0cc02456b

M3 - Article

SN - 1359-7345

VL - 47

SP - 373

EP - 375

JO - Chemical Communications

JF - Chemical Communications

IS - 1

ER -

alpha-Aroyloxyaldehydes: scope and limitations as alternatives to alpha-haloaldehydes for NHC-catalysed redox transformations

Abstract

Keywords

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Projects

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

Cite this