Enzymatic debenzoylation of 1,2-propanediol dibenzoate with 1-octanol has been studied in organic solvent using lipases from different sources. In general a slow, highly regioselective alcoholysis in diisopropyl ether affords exclusively a monoester benzoylated at the secondary hydroxy group although the reaction proceeds with low enantioselectivity. In the presence of Pseudomonas cepacia lipase absorbed onto celite, a faster reaction allows the preparation of the 2-benzoyl ester of (R)-1,2-propanediol (82% ee) and the enantiomerically pure (R)-1-O-benzoyl-2-methylpropane-1,3-diol (>98% ee).

Lipase-catalyzed alcoholysis of diol dibenzoates : Selective enzymatic access to the 2-benzoyl ester of 1,2-propanediol and preparation of the enantiomerically pure (R)-1-O-benzoyl-2-methylpropane-1,3-diol / E. Santaniello, S. Casati, P. Ciuffreda, L. Gamberoni. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 16:9(2005), pp. 1705-1708. [10.1016/j.tetasy.2005.03.019]

Lipase-catalyzed alcoholysis of diol dibenzoates : Selective enzymatic access to the 2-benzoyl ester of 1,2-propanediol and preparation of the enantiomerically pure (R)-1-O-benzoyl-2-methylpropane-1,3-diol

E. Santaniello
Primo
;
S. Casati
Secondo
;
P. Ciuffreda
Penultimo
;
L. Gamberoni
Ultimo
2005

Abstract

Enzymatic debenzoylation of 1,2-propanediol dibenzoate with 1-octanol has been studied in organic solvent using lipases from different sources. In general a slow, highly regioselective alcoholysis in diisopropyl ether affords exclusively a monoester benzoylated at the secondary hydroxy group although the reaction proceeds with low enantioselectivity. In the presence of Pseudomonas cepacia lipase absorbed onto celite, a faster reaction allows the preparation of the 2-benzoyl ester of (R)-1,2-propanediol (82% ee) and the enantiomerically pure (R)-1-O-benzoyl-2-methylpropane-1,3-diol (>98% ee).
KINETIC RESOLUTION; ORGANIC-SYNTHESIS; BENZOYLATION; TRANSESTERIFICATION; CONVENIENT; 1,2-DIOLS; SOLVENTS; ACID
Settore BIO/10 - Biochimica
Settore BIO/10 - Biochimica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/22365
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 13
  • ???jsp.display-item.citation.isi??? 13
social impact