LITHIUM ENEDIOLATES AND DIENEDIOLATES OF CARBOXYLIC-ACIDS IN SYNTHESIS - ALKYLATION WITH SECONDARY HALISDES

Authors
BRUN EM GIL S MESTRES R PARRA M
Citation
Em. Brun et al., LITHIUM ENEDIOLATES AND DIENEDIOLATES OF CARBOXYLIC-ACIDS IN SYNTHESIS - ALKYLATION WITH SECONDARY HALISDES, Tetrahedron, 54(50), 1998, pp. 15305-15320
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
50
Year of publication
1998
Pages
15305 - 15320
Database
ISI
SICI code
0040-4020(1998)54:50<15305:LEADOC>2.0.ZU;2-V
Abstract
High yields in the alkylation of dianions of alpha,beta-unsaturated ca rboxylic acids with secondary halides can be obtained despite eliminat ion reactions occurring. alpha-Regioselectivity for the alkylation of but-2-enoic acids (1-4) is seldom obtained. Although double bond stere oselectivity is higher than 99% for gamma-alkylated products, stereose lectivity is rather poor for most of the alpha-alkylated products. (C) 1998 Elsevier Science Ltd. AII rights reserved.