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Bromine addition to α-(1-hydroxyalkyl)- and α-(1-alkoxy-alkyl)-α,β-unsaturated esters: an approach to hydroxyfimbrolide and bromobeckerelide

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
48
Issue
25
Identifiers
DOI: 10.1016/s0040-4020(01)89031-1

Abstract

Abstract Conventional ionic bromination of electron-poor olefins, 2-(1-hydroxyalkyl)- and 2-(1-alkoxyalkyl)propenoates, 2b-d, and methyl ( E)-2-(1-hydroxyethyl)-2-butenoate, 3a, proceeds with yields higher than 80%. Treatment of ( E)-3-bromo-2-[1-[(2-methoxyethoxy)methoxy]butyl]propenoic acid, 16, with two equivalents of strong bases, reaction related with a possible hydroxyfimbrolide and bromobeckerelide synthesis, resulted in the halogen-metal exchange reaction affording the acrylic acid 18, presumably through the generation of dianion 19.

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