A comparison of the Still-Gennari and Ando HWE-methodologies with alpha,beta-unsaturated aldehydes; unexpected results with stannyl substituted systems

X  Franci; S L X  Martina; J E  McGrady; M R  Webb; C  Donald; R J K  Taylor

doi:10.1016/j.tetlet.2003.08.095

A comparison of the Still-Gennari and Ando HWE-methodologies with alpha,beta-unsaturated aldehydes; unexpected results with stannyl substituted systems

X Franci, S L X Martina, J E McGrady, M R Webb, C Donald, R J K Taylor

Chemistry

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

Abstract

Still-Gennari reactions have been carried out on a range of E- and Z-3-substituted propenals. In all cases, with the exception of Z-3-stannyl systems, good Z-stereoselectivity was observed. By contrast, the Ando procedure gives reasonable Z-stereoselectivity with all systems studied, including those with a cis-disposed stannyl substituent. (C) 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	7735-7740
Number of pages	6
Journal	Tetrahedron Letters
Volume	44
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2003.08.095
Publication status	Published - 13 Oct 2003

Keywords

WADSWORTH-EMMONS REACTION
Z-UNSATURATED ESTERS
HIGHLY SELECTIVE SYNTHESIS
ETHYL (DIARYLPHOSPHONO)ACETATES
WITTIG
STEREOCHEMISTRY
PHOSPHONATE
OLEFINATION
CARBANIONS
REAGENTS

Access to Document

10.1016/j.tetlet.2003.08.095

Cite this

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title = "A comparison of the Still-Gennari and Ando HWE-methodologies with alpha,beta-unsaturated aldehydes; unexpected results with stannyl substituted systems",

abstract = "Still-Gennari reactions have been carried out on a range of E- and Z-3-substituted propenals. In all cases, with the exception of Z-3-stannyl systems, good Z-stereoselectivity was observed. By contrast, the Ando procedure gives reasonable Z-stereoselectivity with all systems studied, including those with a cis-disposed stannyl substituent. (C) 2003 Elsevier Ltd. All rights reserved.",

keywords = "WADSWORTH-EMMONS REACTION, Z-UNSATURATED ESTERS, HIGHLY SELECTIVE SYNTHESIS, ETHYL (DIARYLPHOSPHONO)ACETATES, WITTIG, STEREOCHEMISTRY, PHOSPHONATE, OLEFINATION, CARBANIONS, REAGENTS",

author = "X Franci and Martina, {S L X} and McGrady, {J E} and Webb, {M R} and C Donald and Taylor, {R J K}",

year = "2003",

month = oct,

day = "13",

doi = "10.1016/j.tetlet.2003.08.095",

language = "English",

volume = "44",

pages = "7735--7740",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - A comparison of the Still-Gennari and Ando HWE-methodologies with alpha,beta-unsaturated aldehydes; unexpected results with stannyl substituted systems

AU - Franci, X

AU - Martina, S L X

AU - McGrady, J E

AU - Webb, M R

AU - Donald, C

AU - Taylor, R J K

PY - 2003/10/13

Y1 - 2003/10/13

N2 - Still-Gennari reactions have been carried out on a range of E- and Z-3-substituted propenals. In all cases, with the exception of Z-3-stannyl systems, good Z-stereoselectivity was observed. By contrast, the Ando procedure gives reasonable Z-stereoselectivity with all systems studied, including those with a cis-disposed stannyl substituent. (C) 2003 Elsevier Ltd. All rights reserved.

AB - Still-Gennari reactions have been carried out on a range of E- and Z-3-substituted propenals. In all cases, with the exception of Z-3-stannyl systems, good Z-stereoselectivity was observed. By contrast, the Ando procedure gives reasonable Z-stereoselectivity with all systems studied, including those with a cis-disposed stannyl substituent. (C) 2003 Elsevier Ltd. All rights reserved.

KW - WADSWORTH-EMMONS REACTION

KW - Z-UNSATURATED ESTERS

KW - HIGHLY SELECTIVE SYNTHESIS

KW - ETHYL (DIARYLPHOSPHONO)ACETATES

KW - WITTIG

KW - STEREOCHEMISTRY

KW - PHOSPHONATE

KW - OLEFINATION

KW - CARBANIONS

KW - REAGENTS

U2 - 10.1016/j.tetlet.2003.08.095

DO - 10.1016/j.tetlet.2003.08.095

M3 - Article

SN - 0040-4039

VL - 44

SP - 7735

EP - 7740

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -