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

Angel Calderón; Josep Font; Pedro de March

doi:10.1016/S0040-4020(01)89031-1

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

Angel Calderón, Josep Font, Pedro de March

Department of Chemistry

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

5 Citations (Scopus)

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. © 1992.

Original language	English
Pages (from-to)	5347-5358
Journal	Tetrahedron
Volume	48
Issue number	25
DOIs	https://doi.org/10.1016/S0040-4020(01)89031-1
Publication status	Published - 1 Jan 1992

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@article{19dbd6711de14cac9a9cfe263ecaabba,

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

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. {\textcopyright} 1992.",

author = "Angel Calder{\'o}n and Josep Font and {de March}, Pedro",

year = "1992",

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doi = "10.1016/S0040-4020(01)89031-1",

language = "English",

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pages = "5347--5358",

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T1 - Bromine addition to α-(1-hydroxyalkyl)- and α-(1-alkoxy-alkyl)-α,β-unsaturated esters: an approach to hydroxyfimbrolide and bromobeckerelide

AU - Calderón, Angel

AU - Font, Josep

AU - de March, Pedro

PY - 1992/1/1

Y1 - 1992/1/1

N2 - 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. © 1992.

AB - 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. © 1992.

U2 - 10.1016/S0040-4020(01)89031-1

DO - 10.1016/S0040-4020(01)89031-1

M3 - Article

VL - 48

SP - 5347

EP - 5358

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 25

ER -