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Titolo:
Chemoenzymatic approach toward the pure enantiomers of 2-methyl-1,3-propanediol mono (p-methoxybenzyl ether)
Autore:
Akeboshi, T; Ohtsuka, Y; Ishihara, T; Sugai, T;
Indirizzi:
Keio Univ, Dept Chem, Yokohama, Kanagawa 2238522, Japan Keio Univ Yokohama Kanagawa Japan 2238522 kohama, Kanagawa 2238522, Japan
Titolo Testata:
ADVANCED SYNTHESIS & CATALYSIS
fascicolo: 6-7, volume: 343, anno: 2001,
pagine: 624 - 637
SICI:
1615-4150(200108)343:6-7<624:CATTPE>2.0.ZU;2-D
Fonte:
ISI
Lingua:
ENG
Soggetto:
BETA-HYDROXYISOBUTYRIC ACID; BINAPHTHOL-TITANIUM COMPLEX; PROTECTED SECO ACID; ASYMMETRIC-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE SYNTHESIS; ISOBUTYRIC ACID; BUILDING-BLOCK; HYDROXY ESTERS; EPOTHILONE-B;
Keywords:
chiral building blocks; desymmetrization; hydrolysis; inhibitors; kinetic resolution; lipase; prochiral substrate;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
77
Recensione:
Indirizzi per estratti:
Indirizzo: Sugai, T Keio Univ, Dept Chem, Yokohama, Kanagawa 2238522, Japan Keio Univ Yokohama Kanagawa Japan 2238522 anagawa 2238522, Japan
Citazione:
T. Akeboshi et al., "Chemoenzymatic approach toward the pure enantiomers of 2-methyl-1,3-propanediol mono (p-methoxybenzyl ether)", ADV SYNTH C, 343(6-7), 2001, pp. 624-637

Abstract

In a route towards the enantiomerically pure 2-methylpropane-1,3-diol mono(p-methoxybenzyl ether), which is an important starting material for natural product synthesis, a kinetic resolution approach by means of lipase-catalyzed hydrolysis as well as acylation has been elaborated. Candida antarctica lipase-catalyzed hydrolysis of the corresponding racemic acetate proceeded with high enantioselectivity (E 35). During the studies, a curious phenomenon was observed, namely, that the enantioselectivity gradually declined accompanying the progress of the hydrolysis. This was due to inhibition of the enzyme-catalyzed reaction caused by the accumulation of the resultant alcohol. The rate of reaction of the more reactive enantiomer became lower. This situation prompted a new process, which would minimize the contamination or the undesired enantiomer, prior to the enzyme-catalyzed hydrolysis. This was successfully achieved with the aid of another Pseudomonas cepacia lipase-catalyzed desymmetrization, taking advantage of the prochiral nature of the starting material, 2-methyl-1,3-propanediol, and the subsequent p-methoxybenzylation under mild conditions.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 11/07/20 alle ore 07:31:17