100903-85-3Relevant articles and documents
LITHIUM TRIENOLATE OF SORBIC ACID AS A D6 SYNTHON. SYNTHESIS OF 7-HYDROXY 2,4-DIENOIC ACIDS.
Ballester, P.,Costa, A.,Garcia-Raso, A.,Gomez-Solivellas, A.,Mestres, R.
, p. 3625 - 3628 (1985)
The trienolate 2 of sorbic acid is an easily available d6 synthon.Preparation of 7-hydroxy dienoic acids 5 from ketones is here described.
New Triene Synthesis from Sorbic Acid: Two-Step Synthesis of cis- and trans-Galbanolenes
Fehr, Charles,Galindo, Jose,Chappuis, Simone
, p. 2465 - 2468 (2007/10/02)
The lithium dianion of sorbic acid reacts with hexanal at the C(2)-position to afford separable anti- and syn-hydroxy carboxylic acids 3 and 4 (87percent; 3/4=59:41 or 79percent; 3/4=16:84), whose stereospecific anti-decarboxylative elimination respectively affords (3E,5Z)- and (3E,5E)-1,3,5-undecatriene (1) and (2) (cis- and trans-galbanolenes (1) and (2) (69percent).An alternative route to 1 involves conversion of 3,4 to cis-lactone 7 (45percent after chromatography) followed by thermal syn-decarboxylation (81percent).The described procedure is both new and of general applicability, as illustrated by the synthesis of trienes with different substitution pattern.Key Words: Sorbic acid; aldol reaction; triene synthesis; olefination; decarboxylative elimination.
UNSATURATED CARBOXYLIC ACID POLYENOLATES. LITHIUM TRIENOLATE OF SORBIC ACID AS d6 SYNTHON: ADDITION TO KETONES AND UNSATURATED KETONES
Ballester, Pablo,Costa, Antonio,Garcia-Raso, Angel,Mestres, Ramon
, p. 2797 - 2804 (2007/10/02)
Deprotonation of sorbic acid by two equivalents of lithium diethylamide, and aldol-type reaction of the resulting trienolate dianion (2) with carbonylic compounds affords the pentadienyl hydroxy acids (6) or 7-hydroxyhexa-2,4-dienoic acids (7) according to the duration of the reaction.The reaction of the dianion (2) with α,β-unsaturated ketones gives 1,4-ε-adducts for di- or tri-substituted enones, but either 1,4-γ- or 1,4-α-adducts for monosubstituted enones.