TY - JOUR
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 -