102-22-7Relevant articles and documents
Gd(OTf)3-catalyzed synthesis of geranyl esters for the intramolecular radical cyclization of their epoxides mediated by titanocene(III)
Garca Santos, William H.,Puerto Galvis, Carlos E.,Kouznetsov, Vladimir V.
, p. 1358 - 1366 (2015)
A selective and mild method for the esterification of a variety of carboxylic acids with geraniol is developed. We demonstrated that the use of triphenylphosphine, I2, 2-methylimidazole or imidazole and a catalytic amount of Gd(OTf)3 resulted to be more active than the previous protocols, providing a 16-membered library of geranyl esters in higher yields and in shorter reaction times. The use of essential oil of palmarosa (Cymbopogon martinii), enriched with geraniol, as a raw material for the synthesis of the target compounds complemented and proved how sustainable and eco-friendly this protocol is. Finally, the selective 6,7-epoxidation of the obtained geranyl esters led us to study their regio-controlled radical cyclization mediated by titanocene(iii) for the synthesis of novel (8-hydroxy-9,9-dimethyl-5-methylene cyclohexyl)methyl esters in moderate yields and with excellent stereoselectivities.
A USEFUL METHOD FOR SELECTIVE ACYLATION OF ALCOHOLS USING 2,2'-BIPYRIDYL-6-YL CARBOXYLATE AND CESIUM FLUORIDE
Mukaiyama, Teruaki,Pai, Fong-Chang,Onaka, Makoto,Narasaka, Koichi
, p. 563 - 566 (2007/10/02)
Primary and secondary alcohols are acylated under mild conditions by the of use 2,2'-bipyridyl-6-yl carboxylates and cesium fluoride.Furthermore, the reaction is successfully applied to selective acylation of a primary carbinol group of diols containing primary and secondary carbinol groups or exclusive O-acylation of aromatic amino alcohols.