Stereoselective aldol coupling of α,β-acetylenic ketones promoted by MgI2

Han Xun Wei; Jiali Hu; David W. Purkiss; Paul W. Paré

doi:10.1016/S0040-4039(02)02746-6

Stereoselective aldol coupling of α,β-acetylenic ketones promoted by MgI₂

Han Xun Wei, Jiali Hu, David W. Purkiss, Paul W. Paré

Chemistry and Biochemistry

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

35 Scopus citations

Abstract

A highly stereoselective synthesis of (Z)-β-iodovinyl ketone has been achieved with the tandem formation of C-C and C-I bonds in a three-component reaction. This new catalysis utilizes MgI₂ as a Lewis acid as well as an iodine source for a Michael-type addition. α,β-Acetylenic ketone is initially converted to an active β-iodo allenolate intermediate and then can be attacked by a variety of aldehydes to afford Z-selective Baylis-Hillman adducts in excellent yields.

Original language	English
Pages (from-to)	949-952
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	5
DOIs	https://doi.org/10.1016/S0040-4039(02)02746-6
State	Published - Jan 27 2003

Keywords

(Z)-β-iodovinyl ketone
Baylis-Hillman adducts
Magnesium iodide
α,β-acetylenic ketones

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10.1016/S0040-4039(02)02746-6

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title = "Stereoselective aldol coupling of α,β-acetylenic ketones promoted by MgI2",

abstract = "A highly stereoselective synthesis of (Z)-β-iodovinyl ketone has been achieved with the tandem formation of C-C and C-I bonds in a three-component reaction. This new catalysis utilizes MgI2 as a Lewis acid as well as an iodine source for a Michael-type addition. α,β-Acetylenic ketone is initially converted to an active β-iodo allenolate intermediate and then can be attacked by a variety of aldehydes to afford Z-selective Baylis-Hillman adducts in excellent yields.",

keywords = "(Z)-β-iodovinyl ketone, Baylis-Hillman adducts, Magnesium iodide, α,β-acetylenic ketones",

author = "Wei, {Han Xun} and Jiali Hu and Purkiss, {David W.} and Par{\'e}, {Paul W.}",

note = "Funding Information: Financial support was provided by the Robert A. Welch Foundation (Grant # D-1478).",

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T1 - Stereoselective aldol coupling of α,β-acetylenic ketones promoted by MgI2

AU - Wei, Han Xun

AU - Hu, Jiali

AU - Purkiss, David W.

AU - Paré, Paul W.

N1 - Funding Information: Financial support was provided by the Robert A. Welch Foundation (Grant # D-1478).

PY - 2003/1/27

Y1 - 2003/1/27

N2 - A highly stereoselective synthesis of (Z)-β-iodovinyl ketone has been achieved with the tandem formation of C-C and C-I bonds in a three-component reaction. This new catalysis utilizes MgI2 as a Lewis acid as well as an iodine source for a Michael-type addition. α,β-Acetylenic ketone is initially converted to an active β-iodo allenolate intermediate and then can be attacked by a variety of aldehydes to afford Z-selective Baylis-Hillman adducts in excellent yields.

AB - A highly stereoselective synthesis of (Z)-β-iodovinyl ketone has been achieved with the tandem formation of C-C and C-I bonds in a three-component reaction. This new catalysis utilizes MgI2 as a Lewis acid as well as an iodine source for a Michael-type addition. α,β-Acetylenic ketone is initially converted to an active β-iodo allenolate intermediate and then can be attacked by a variety of aldehydes to afford Z-selective Baylis-Hillman adducts in excellent yields.

KW - (Z)-β-iodovinyl ketone

KW - Baylis-Hillman adducts

KW - Magnesium iodide

KW - α,β-acetylenic ketones

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U2 - 10.1016/S0040-4039(02)02746-6

DO - 10.1016/S0040-4039(02)02746-6

M3 - Article

AN - SCOPUS:0037467815

SN - 0040-4039

VL - 44

SP - 949

EP - 952

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

Stereoselective aldol coupling of α,β-acetylenic ketones promoted by MgI₂

Abstract

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