New solid-supported phosphonate reagents for the synthesis of Z-alpha,beta-unsaturated esters

S L X  Martina; R J K  Taylor

doi:10.1016/j.tetlet.2004.02.138

New solid-supported phosphonate reagents for the synthesis of Z-alpha,beta-unsaturated esters

S L X Martina, R J K Taylor

Chemistry

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

Abstract

Novel solid-supported phosphonate reagents have been prepared and evaluated for the synthesis of alpha,beta-unsaturated esters with a preference for the Z-alkene. The optimal reagent was a hybrid of both Still-Gennari and Ando reagents, and showed good to high yields and fair to good Z-selectivity for the conversion of both aliphatic and aromatic aldehydes. (C) 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3279-3282
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2004.02.138
Publication status	Published - 12 Apr 2004

Keywords

solid supported
ando
Still-Gennari
Horner-Wadsworth-Emmons
WADSWORTH-EMMONS REACTION
Z-UNSATURATED ESTERS
MULTISTEP ORGANIC-SYNTHESIS
PHASE SYNTHESIS
ETHYL (DIARYLPHOSPHONO)ACETATES
ALDEHYDES
LIBRARY
OLEFINATION
SELECTIVITY
CONVERSION

Access to Document

10.1016/j.tetlet.2004.02.138

Cite this

@article{99f1993339274125af8dbb37f919efa9,

title = "New solid-supported phosphonate reagents for the synthesis of Z-alpha,beta-unsaturated esters",

abstract = "Novel solid-supported phosphonate reagents have been prepared and evaluated for the synthesis of alpha,beta-unsaturated esters with a preference for the Z-alkene. The optimal reagent was a hybrid of both Still-Gennari and Ando reagents, and showed good to high yields and fair to good Z-selectivity for the conversion of both aliphatic and aromatic aldehydes. (C) 2004 Elsevier Ltd. All rights reserved.",

keywords = "solid supported, ando, Still-Gennari, Horner-Wadsworth-Emmons, WADSWORTH-EMMONS REACTION, Z-UNSATURATED ESTERS, MULTISTEP ORGANIC-SYNTHESIS, PHASE SYNTHESIS, ETHYL (DIARYLPHOSPHONO)ACETATES, ALDEHYDES, LIBRARY, OLEFINATION, SELECTIVITY, CONVERSION",

author = "Martina, {S L X} and Taylor, {R J K}",

year = "2004",

month = apr,

day = "12",

doi = "10.1016/j.tetlet.2004.02.138",

language = "English",

volume = "45",

pages = "3279--3282",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "16",

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TY - JOUR

T1 - New solid-supported phosphonate reagents for the synthesis of Z-alpha,beta-unsaturated esters

AU - Martina, S L X

AU - Taylor, R J K

PY - 2004/4/12

Y1 - 2004/4/12

N2 - Novel solid-supported phosphonate reagents have been prepared and evaluated for the synthesis of alpha,beta-unsaturated esters with a preference for the Z-alkene. The optimal reagent was a hybrid of both Still-Gennari and Ando reagents, and showed good to high yields and fair to good Z-selectivity for the conversion of both aliphatic and aromatic aldehydes. (C) 2004 Elsevier Ltd. All rights reserved.

AB - Novel solid-supported phosphonate reagents have been prepared and evaluated for the synthesis of alpha,beta-unsaturated esters with a preference for the Z-alkene. The optimal reagent was a hybrid of both Still-Gennari and Ando reagents, and showed good to high yields and fair to good Z-selectivity for the conversion of both aliphatic and aromatic aldehydes. (C) 2004 Elsevier Ltd. All rights reserved.

KW - solid supported

KW - ando

KW - Still-Gennari

KW - Horner-Wadsworth-Emmons

KW - WADSWORTH-EMMONS REACTION

KW - Z-UNSATURATED ESTERS

KW - MULTISTEP ORGANIC-SYNTHESIS

KW - PHASE SYNTHESIS

KW - ETHYL (DIARYLPHOSPHONO)ACETATES

KW - ALDEHYDES

KW - LIBRARY

KW - OLEFINATION

KW - SELECTIVITY

KW - CONVERSION

U2 - 10.1016/j.tetlet.2004.02.138

DO - 10.1016/j.tetlet.2004.02.138

M3 - Article

SN - 0040-4039

VL - 45

SP - 3279

EP - 3282

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -