A new stereospecific synthesis of unusual (Z)-β-branched Baylis- Hillman adducts

Guigen Li; Han Xun Wei; Steven Willis

doi:10.1016/S0040-4039(98)00850-8

A new stereospecific synthesis of unusual (Z)-β-branched Baylis- Hillman adducts

Guigen Li, Han Xun Wei, Steven Willis

Chemistry and Biochemistry

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Abstract

A new method has been developed for the stereospecific synthesis of unusual (Z)-β-branched Baylis-Hillman adducts with high Z/E selectivity (>99 %) in modest to good yields. The process involves successful formation of anionic β-substituted [α-(alkoxycarbonyl)vinyl]aluminum intermediates and their coupling with aldehydes and ketones catalyzed by n-Bu₂BOTf at -78°C.

Original language	English
Pages (from-to)	4607-4610
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4039(98)00850-8
State	Published - Jun 25 1998

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title = "A new stereospecific synthesis of unusual (Z)-β-branched Baylis- Hillman adducts",

abstract = "A new method has been developed for the stereospecific synthesis of unusual (Z)-β-branched Baylis-Hillman adducts with high Z/E selectivity (>99 %) in modest to good yields. The process involves successful formation of anionic β-substituted [α-(alkoxycarbonyl)vinyl]aluminum intermediates and their coupling with aldehydes and ketones catalyzed by n-Bu2BOTf at -78°C.",

author = "Guigen Li and Wei, {Han Xun} and Steven Willis",

note = "Funding Information: Acknowledgments We gratefully acknowledge financial support from the Robert A. Welch Foundation (grant",

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AU - Li, Guigen

AU - Wei, Han Xun

AU - Willis, Steven

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PY - 1998/6/25

Y1 - 1998/6/25

N2 - A new method has been developed for the stereospecific synthesis of unusual (Z)-β-branched Baylis-Hillman adducts with high Z/E selectivity (>99 %) in modest to good yields. The process involves successful formation of anionic β-substituted [α-(alkoxycarbonyl)vinyl]aluminum intermediates and their coupling with aldehydes and ketones catalyzed by n-Bu2BOTf at -78°C.

AB - A new method has been developed for the stereospecific synthesis of unusual (Z)-β-branched Baylis-Hillman adducts with high Z/E selectivity (>99 %) in modest to good yields. The process involves successful formation of anionic β-substituted [α-(alkoxycarbonyl)vinyl]aluminum intermediates and their coupling with aldehydes and ketones catalyzed by n-Bu2BOTf at -78°C.

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U2 - 10.1016/S0040-4039(98)00850-8

DO - 10.1016/S0040-4039(98)00850-8

M3 - Article

AN - SCOPUS:0032565841

SN - 0040-4039

VL - 39

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EP - 4610

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

A new stereospecific synthesis of unusual (Z)-β-branched Baylis- Hillman adducts

Abstract

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