Highly (E)-Selective Wadsworth-Emmons Reactions Promoted by Methylmagnesium Bromide

Timothy D. W. Claridge; Stephen G. Davies; James A. Lee; Rebecca L. Nicholson; Paul M. Roberts; Angela J. Russell; Andrew D. Smith; Steven M. Toms

doi:10.1021/ol802212e

Highly (E)-Selective Wadsworth-Emmons Reactions Promoted by Methylmagnesium Bromide

Timothy D. W. Claridge
, Stephen G. Davies
, James A. Lee
, Rebecca L. Nicholson
, Paul M. Roberts
, Angela J. Russell
, Andrew D. Smith
, Steven M. Toms

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

Abstract

An experimentally simple protocol for the very highly (E)-selective Wadsworth-Emmons reaction [(E):(Z) selectivities in excess of 180:1 in some cases] of a range of straight-chain and branched aliphatic, substituted aromatic, and base-sensitive aldehydes via reaction with an alkyl diethylphosphonoacetate and MeMgBr is reported.

Original language	English
Pages (from-to)	5437-5440
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	23
DOIs	https://doi.org/10.1021/ol802212e
Publication status	Published - 4 Dec 2008

Keywords

LATENT ALDEHYDE EQUIVALENTS
BETA-AMINO ACIDS
ASYMMETRIC-SYNTHESIS
ETHYL (DIARYLPHOSPHONO)ACETATES
OLEFINATION REACTION
CARBONYL-COMPOUNDS
ESTERS
LITHIUM
CONSTRUCTION
DERIVATIVES

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@article{b7b3f06aa955416aa96983a5c2c78a41,

title = "Highly (E)-Selective Wadsworth-Emmons Reactions Promoted by Methylmagnesium Bromide",

abstract = "An experimentally simple protocol for the very highly (E)-selective Wadsworth-Emmons reaction [(E):(Z) selectivities in excess of 180:1 in some cases] of a range of straight-chain and branched aliphatic, substituted aromatic, and base-sensitive aldehydes via reaction with an alkyl diethylphosphonoacetate and MeMgBr is reported.",

keywords = "LATENT ALDEHYDE EQUIVALENTS, BETA-AMINO ACIDS, ASYMMETRIC-SYNTHESIS, ETHYL (DIARYLPHOSPHONO)ACETATES, OLEFINATION REACTION, CARBONYL-COMPOUNDS, ESTERS, LITHIUM, CONSTRUCTION, DERIVATIVES",

author = "Claridge, \{Timothy D. W.\} and Davies, \{Stephen G.\} and Lee, \{James A.\} and Nicholson, \{Rebecca L.\} and Roberts, \{Paul M.\} and Russell, \{Angela J.\} and Smith, \{Andrew D.\} and Toms, \{Steven M.\}",

year = "2008",

month = dec,

day = "4",

doi = "10.1021/ol802212e",

language = "English",

volume = "10",

pages = "5437--5440",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "23",

}

TY - JOUR

T1 - Highly (E)-Selective Wadsworth-Emmons Reactions Promoted by Methylmagnesium Bromide

AU - Claridge, Timothy D. W.

AU - Davies, Stephen G.

AU - Lee, James A.

AU - Nicholson, Rebecca L.

AU - Roberts, Paul M.

AU - Russell, Angela J.

AU - Smith, Andrew D.

AU - Toms, Steven M.

PY - 2008/12/4

Y1 - 2008/12/4

N2 - An experimentally simple protocol for the very highly (E)-selective Wadsworth-Emmons reaction [(E):(Z) selectivities in excess of 180:1 in some cases] of a range of straight-chain and branched aliphatic, substituted aromatic, and base-sensitive aldehydes via reaction with an alkyl diethylphosphonoacetate and MeMgBr is reported.

AB - An experimentally simple protocol for the very highly (E)-selective Wadsworth-Emmons reaction [(E):(Z) selectivities in excess of 180:1 in some cases] of a range of straight-chain and branched aliphatic, substituted aromatic, and base-sensitive aldehydes via reaction with an alkyl diethylphosphonoacetate and MeMgBr is reported.

KW - LATENT ALDEHYDE EQUIVALENTS

KW - BETA-AMINO ACIDS

KW - ASYMMETRIC-SYNTHESIS

KW - ETHYL (DIARYLPHOSPHONO)ACETATES

KW - OLEFINATION REACTION

KW - CARBONYL-COMPOUNDS

KW - ESTERS

KW - LITHIUM

KW - CONSTRUCTION

KW - DERIVATIVES

U2 - 10.1021/ol802212e

DO - 10.1021/ol802212e

M3 - Article

SN - 1523-7060

VL - 10

SP - 5437

EP - 5440

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Highly (E)-Selective Wadsworth-Emmons Reactions Promoted by Methylmagnesium Bromide

Abstract

Keywords

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