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

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)1765-1773
Number of pages9
JournalSynthetic Communications
Volume32
Issue number11
DOIs
StatePublished - 2002

Fingerprint

Dive into the research topics of 'Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones via a one-pot three-component X-C/C-C formation reaction'. Together they form a unique fingerprint.

Cite this