Synthesis of β-iodo-α-(hydroxyalkyl)acrylates: A convenient and stereoselective reaction

Han Xun Wei; Guigen Li; Joe J. Gao; Paul W. Paré

doi:10.1016/S0040-4039(02)01106-1

Synthesis of β-iodo-α-(hydroxyalkyl)acrylates: A convenient and stereoselective reaction

Han Xun Wei, Guigen Li, Joe J. Gao, Paul W. Paré

Chemistry and Biochemistry

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

31 Scopus citations

Abstract

An efficient one-pot, three-component coupling reaction for the synthesis of β-iodo-α-(hydroxyalkyl) acrylates has been developed. As the iodine source as well as the Lewis acid mediator, diethyl aluminium iodide undergoes a Michael-type addition with methyl propynoate to form an active β-iodo allenolate intermediate, which in turn attacks various aldehydes or ketones to afford β-iodo Baylis-Hillman adducts in excellent yields with high Z-selectivity.

Original language	English
Pages (from-to)	5677-5680
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4039(02)01106-1
State	Published - Aug 5 2002

Keywords

Baylis-Hillman adducts
Diethyl aluminium iodide
Methyl propynoate
β-iodo-α-(hydroxyalkyl)acrylates

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10.1016/S0040-4039(02)01106-1

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title = "Synthesis of β-iodo-α-(hydroxyalkyl)acrylates: A convenient and stereoselective reaction",

abstract = "An efficient one-pot, three-component coupling reaction for the synthesis of β-iodo-α-(hydroxyalkyl) acrylates has been developed. As the iodine source as well as the Lewis acid mediator, diethyl aluminium iodide undergoes a Michael-type addition with methyl propynoate to form an active β-iodo allenolate intermediate, which in turn attacks various aldehydes or ketones to afford β-iodo Baylis-Hillman adducts in excellent yields with high Z-selectivity.",

keywords = "Baylis-Hillman adducts, Diethyl aluminium iodide, Methyl propynoate, β-iodo-α-(hydroxyalkyl)acrylates",

author = "Wei, {Han Xun} and Guigen Li and Gao, {Joe J.} and Par{\'e}, {Paul W.}",

note = "Funding Information: We thank D. Purkiss for expert NMR support. Financial support was provided by the Robert A Welch Foundation (D-1478 and D-1361). ",

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T1 - Synthesis of β-iodo-α-(hydroxyalkyl)acrylates

T2 - A convenient and stereoselective reaction

AU - Wei, Han Xun

AU - Li, Guigen

AU - Gao, Joe J.

AU - Paré, Paul W.

N1 - Funding Information: We thank D. Purkiss for expert NMR support. Financial support was provided by the Robert A Welch Foundation (D-1478 and D-1361).

PY - 2002/8/5

Y1 - 2002/8/5

N2 - An efficient one-pot, three-component coupling reaction for the synthesis of β-iodo-α-(hydroxyalkyl) acrylates has been developed. As the iodine source as well as the Lewis acid mediator, diethyl aluminium iodide undergoes a Michael-type addition with methyl propynoate to form an active β-iodo allenolate intermediate, which in turn attacks various aldehydes or ketones to afford β-iodo Baylis-Hillman adducts in excellent yields with high Z-selectivity.

AB - An efficient one-pot, three-component coupling reaction for the synthesis of β-iodo-α-(hydroxyalkyl) acrylates has been developed. As the iodine source as well as the Lewis acid mediator, diethyl aluminium iodide undergoes a Michael-type addition with methyl propynoate to form an active β-iodo allenolate intermediate, which in turn attacks various aldehydes or ketones to afford β-iodo Baylis-Hillman adducts in excellent yields with high Z-selectivity.

KW - Baylis-Hillman adducts

KW - Diethyl aluminium iodide

KW - Methyl propynoate

KW - β-iodo-α-(hydroxyalkyl)acrylates

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U2 - 10.1016/S0040-4039(02)01106-1

DO - 10.1016/S0040-4039(02)01106-1

M3 - Article

AN - SCOPUS:0037025782

SN - 0040-4039

VL - 43

SP - 5677

EP - 5680

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Synthesis of β-iodo-α-(hydroxyalkyl)acrylates: A convenient and stereoselective reaction

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