ENZYMATIC ESTERIFICATION OF BICYCLIC MESO-DIOLS DERIVED FROM 1,4-BIS(HYDROXYMETHYL)FURAN - AN ENANTIOSELECTIVE DIELS-ALDER REACTION EQUIVALENT

Authors
ANDREU C VILLARROYA JP GARCIAGASTALDI A MEDIOSIMON M SERVERCARRIO J VAREA T
Citation
C. Andreu et al., ENZYMATIC ESTERIFICATION OF BICYCLIC MESO-DIOLS DERIVED FROM 1,4-BIS(HYDROXYMETHYL)FURAN - AN ENANTIOSELECTIVE DIELS-ALDER REACTION EQUIVALENT, Tetrahedron : asymmetry, 9(17), 1998, pp. 3105-3114
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
17
Year of publication
1998
Pages
3105 - 3114
Database
ISI
SICI code
0957-4166(1998)9:17<3105:EEOBMD>2.0.ZU;2-W
Abstract
meso-Diols derived from the Diels-Alder adduct 1,4-bis(hydroxymethyl)f uran/dimethyl acetylenedicarboxylate can be enantioselectively monoace tylated under CRL or PSL catalysis with very good yields and moderate to excellent ees. (+)-Monoacetates are always preferentially formed in the reactions catalyzed by CRL, and their (-)-enantiomers are the mai n products in the acetylations under PSL catalysis. Absolute configura tions have been determined by X-ray analysis of a single crystal of an (R)-alpha-methoxyphenylacetyl derivative. (C) 1998 Elsevier Science L td. All rights reserved.