Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones via a one-pot three-component X-C/C-C formation reaction

Guigen Li; Han Xun Wei; Joe J. Gao; Jeremy Johnson

doi:10.1081/SCC-120004273

Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones via a one-pot three-component X-C/C-C formation reaction

Guigen Li, Han Xun Wei, Joe J. Gao, Jeremy Johnson

Chemistry and Biochemistry

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

14 Scopus citations

Abstract

Highly stereoselective synthesis of (E)-β-bromo Baylis Hillman ketones has been achieved using a three-component X-C/C-C formation reaction. The synthesis involves the Michael-type addition of TiBr₄ to α,β-acetylenic ketones without using any bases and carbonyl coupling with aldehydes. Modest yields (50-65%) and complete E/Z geometric selectivity have been realized for 10 examples.

Original language	English
Pages (from-to)	1765-1773
Number of pages	9
Journal	Synthetic Communications
Volume	32
Issue number	11
DOIs	https://doi.org/10.1081/SCC-120004273
State	Published - 2002

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title = "Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones via a one-pot three-component X-C/C-C formation reaction",

abstract = "Highly stereoselective synthesis of (E)-β-bromo Baylis Hillman ketones has been achieved using a three-component X-C/C-C formation reaction. The synthesis involves the Michael-type addition of TiBr4 to α,β-acetylenic ketones without using any bases and carbonyl coupling with aldehydes. Modest yields (50-65%) and complete E/Z geometric selectivity have been realized for 10 examples.",

author = "Guigen Li and Wei, {Han Xun} and Gao, {Joe J.} and Jeremy Johnson",

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T1 - Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones via a one-pot three-component X-C/C-C formation reaction

AU - Li, Guigen

AU - Wei, Han Xun

AU - Gao, Joe J.

AU - Johnson, Jeremy

PY - 2002

Y1 - 2002

N2 - Highly stereoselective synthesis of (E)-β-bromo Baylis Hillman ketones has been achieved using a three-component X-C/C-C formation reaction. The synthesis involves the Michael-type addition of TiBr4 to α,β-acetylenic ketones without using any bases and carbonyl coupling with aldehydes. Modest yields (50-65%) and complete E/Z geometric selectivity have been realized for 10 examples.

AB - Highly stereoselective synthesis of (E)-β-bromo Baylis Hillman ketones has been achieved using a three-component X-C/C-C formation reaction. The synthesis involves the Michael-type addition of TiBr4 to α,β-acetylenic ketones without using any bases and carbonyl coupling with aldehydes. Modest yields (50-65%) and complete E/Z geometric selectivity have been realized for 10 examples.

UR - http://www.scopus.com/inward/record.url?scp=0036293008&partnerID=8YFLogxK

U2 - 10.1081/SCC-120004273

DO - 10.1081/SCC-120004273

M3 - Article

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SP - 1765

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JO - Synthetic Communications

JF - Synthetic Communications

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