GAMMA-ALKYLATION OF UNSATURATED CARBOXYLIC-ACIDS - STEREOSELECTIVE SYNTHESIS OF 2Z-6E-3-METHYLDECA-2-6-DIENOIC AND 2E-6E-3-METHYLDECA-2-6-DIENOIC ACIDS FROM 3-METHLBUT-2-ENOIC ACID THROUGH CONSECUTIVE IRELAND CLAISEN AND COPE REARRANGEMENTS

Authors
GIL S LAZARO MA PARRA M BREITMAIER E MESTRES R
Citation
S. Gil et al., GAMMA-ALKYLATION OF UNSATURATED CARBOXYLIC-ACIDS - STEREOSELECTIVE SYNTHESIS OF 2Z-6E-3-METHYLDECA-2-6-DIENOIC AND 2E-6E-3-METHYLDECA-2-6-DIENOIC ACIDS FROM 3-METHLBUT-2-ENOIC ACID THROUGH CONSECUTIVE IRELAND CLAISEN AND COPE REARRANGEMENTS, Synlett, (1), 1998, pp. 70
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
1
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):1<70:GOUC-S>2.0.ZU;2-3
Abstract
gamma-Alkylation of 3-methyl-2-butenoic acid is attained by consecutiv e Ireland Claisen and Cope rearrangements of its allylic alcohol ester s. With E- and-Z-2-hexen-1-ol, alkylation occurs sterospecifically wit h inverted transfer of configuration from the alcohol to the acid moie ty, to give 2Z,6E- and 2E,6E-3-methyl-2,6-decadienoic acids, repective ly.