Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones using MgBr 2 as promoter via a one-pot three-component reaction

Han Xun Wei; Richard L. Jasoni; Jiali Hu; Guigen Li; Paul W. Paré

doi:10.1016/j.tet.2004.08.097

Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones using MgBr ₂ as promoter via a one-pot three-component reaction

Han Xun Wei, Richard L. Jasoni, Jiali Hu, Guigen Li, Paul W. Paré

Chemistry and Biochemistry

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

24 Scopus citations

Abstract

The first time steroselective synthesis of (Z)-β-bromo Baylis-Hillman ketones has been achieved using a one-pot three-component reaction. The new system uses MgBr ₂ as both the Lewis acidic promoter and the bromine source for the Michael-type addition with α,β-acetylenic ketones to form an active β-bromo allenolate intermediate, which in turn attacks various aldehydes to afford β-bromo Baylis-Hillman adducts in good yields and Z-selectivity. Graphical Abstract

Original language	English
Pages (from-to)	10233-10237
Number of pages	5
Journal	Tetrahedron
Volume	60
Issue number	45
DOIs	https://doi.org/10.1016/j.tet.2004.08.097
State	Published - Nov 1 2004

Keywords

(Z)-β-Bromovinyl ketone
Baylis-Hillman adducts
Magnesium bromine
α,β-Acetylenic ketones

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10.1016/j.tet.2004.08.097

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title = "Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones using MgBr 2 as promoter via a one-pot three-component reaction",

abstract = "The first time steroselective synthesis of (Z)-β-bromo Baylis-Hillman ketones has been achieved using a one-pot three-component reaction. The new system uses MgBr 2 as both the Lewis acidic promoter and the bromine source for the Michael-type addition with α,β-acetylenic ketones to form an active β-bromo allenolate intermediate, which in turn attacks various aldehydes to afford β-bromo Baylis-Hillman adducts in good yields and Z-selectivity. Graphical Abstract",

keywords = "(Z)-β-Bromovinyl ketone, Baylis-Hillman adducts, Magnesium bromine, α,β-Acetylenic ketones",

author = "Wei, {Han Xun} and Jasoni, {Richard L.} and Jiali Hu and Guigen Li and Par{\'e}, {Paul W.}",

note = "Funding Information: We thank D. Purkiss for expert NMR technical support. The Robert A. Welch Foundation (D-1478 and D-1361) provided financial assistance.",

year = "2004",

month = nov,

day = "1",

doi = "10.1016/j.tet.2004.08.097",

language = "English",

volume = "60",

pages = "10233--10237",

journal = "Tetrahedron",

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TY - JOUR

T1 - Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones using MgBr 2 as promoter via a one-pot three-component reaction

AU - Wei, Han Xun

AU - Jasoni, Richard L.

AU - Hu, Jiali

AU - Li, Guigen

AU - Paré, Paul W.

N1 - Funding Information: We thank D. Purkiss for expert NMR technical support. The Robert A. Welch Foundation (D-1478 and D-1361) provided financial assistance.

PY - 2004/11/1

Y1 - 2004/11/1

N2 - The first time steroselective synthesis of (Z)-β-bromo Baylis-Hillman ketones has been achieved using a one-pot three-component reaction. The new system uses MgBr 2 as both the Lewis acidic promoter and the bromine source for the Michael-type addition with α,β-acetylenic ketones to form an active β-bromo allenolate intermediate, which in turn attacks various aldehydes to afford β-bromo Baylis-Hillman adducts in good yields and Z-selectivity. Graphical Abstract

AB - The first time steroselective synthesis of (Z)-β-bromo Baylis-Hillman ketones has been achieved using a one-pot three-component reaction. The new system uses MgBr 2 as both the Lewis acidic promoter and the bromine source for the Michael-type addition with α,β-acetylenic ketones to form an active β-bromo allenolate intermediate, which in turn attacks various aldehydes to afford β-bromo Baylis-Hillman adducts in good yields and Z-selectivity. Graphical Abstract

KW - (Z)-β-Bromovinyl ketone

KW - Baylis-Hillman adducts

KW - Magnesium bromine

KW - α,β-Acetylenic ketones

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U2 - 10.1016/j.tet.2004.08.097

DO - 10.1016/j.tet.2004.08.097

M3 - Article

AN - SCOPUS:4644359367

SN - 0040-4020

VL - 60

SP - 10233

EP - 10237

JO - Tetrahedron

JF - Tetrahedron

IS - 45

ER -

Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones using MgBr ₂ as promoter via a one-pot three-component reaction

Abstract

Keywords

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