Effect of amines on the selective bromination of some β-substituted-2- butenoic esters

Masahisa Nakada, Ei Ichi Kojima, Hidehiro Ichinose

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Abstract

The effect of amines on the selective bromination of some β- substituted-2-butenoic esters is described. The bromination of methyl (Z)4-t- butyldiphenylsilyloxy-3-methylbutenoate 2 in the presence of DIPEA (N, N- diisopropylethylamine) and the successive treatment of the obtained dibromide with potassium t-butoxide afford the desired Z bromide selectively. But the corresponding E bromide forms exclusively when 2, 6-di-t-butyl-4- methylpyridine is used in the bromination.

Original languageEnglish
Pages (from-to)863-868
Number of pages6
JournalSynthetic Communications
Volume30
Issue number5
Publication statusPublished - 2000
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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