Sila-morita-baylis-hillman reaction of Arylvinyl ketones: Overcoming the dimerization problem

Alexander Trofimov; Vladimir Gevorgyan

doi:10.1021/ol8026522

Sila-morita-baylis-hillman reaction of Arylvinyl ketones: Overcoming the dimerization problem

Alexander Trofimov, Vladimir Gevorgyan

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

27 Scopus citations

Abstract

Arylvinyl ketones, under Morita-Baylis-Hillman (MBH) reaction conditions, produce a mixture of dimerization products. We propose a solution to this problem: a sila-MBH reaction. This cascade reaction involves addition of phosphine catalyst to arylvinyl ketones, trapping of the forming β-silylenolate with aldehyde, followed by a 1,3-Brook rearrangement to give the Si-MBH adducts in good to excellent yields.

Original language	English (US)
Pages (from-to)	253-255
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	1
DOIs	https://doi.org/10.1021/ol8026522
State	Published - Jan 1 2009
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol8026522

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abstract = "Arylvinyl ketones, under Morita-Baylis-Hillman (MBH) reaction conditions, produce a mixture of dimerization products. We propose a solution to this problem: a sila-MBH reaction. This cascade reaction involves addition of phosphine catalyst to arylvinyl ketones, trapping of the forming β-silylenolate with aldehyde, followed by a 1,3-Brook rearrangement to give the Si-MBH adducts in good to excellent yields.",

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AU - Gevorgyan, Vladimir

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N2 - Arylvinyl ketones, under Morita-Baylis-Hillman (MBH) reaction conditions, produce a mixture of dimerization products. We propose a solution to this problem: a sila-MBH reaction. This cascade reaction involves addition of phosphine catalyst to arylvinyl ketones, trapping of the forming β-silylenolate with aldehyde, followed by a 1,3-Brook rearrangement to give the Si-MBH adducts in good to excellent yields.

AB - Arylvinyl ketones, under Morita-Baylis-Hillman (MBH) reaction conditions, produce a mixture of dimerization products. We propose a solution to this problem: a sila-MBH reaction. This cascade reaction involves addition of phosphine catalyst to arylvinyl ketones, trapping of the forming β-silylenolate with aldehyde, followed by a 1,3-Brook rearrangement to give the Si-MBH adducts in good to excellent yields.

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Sila-morita-baylis-hillman reaction of Arylvinyl ketones: Overcoming the dimerization problem

Abstract

ASJC Scopus subject areas

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