Lipase-mediated synthesis of the enantiomeric forms of 4,5-epoxy-4,5-dihydro-alpha-ionone and 5,6-epoxy-5,6-dihydro-beta-ionone. A new direct access to enantiopure (R)- and (S)-alpha-ionone

Citation
J. Aleu et al., Lipase-mediated synthesis of the enantiomeric forms of 4,5-epoxy-4,5-dihydro-alpha-ionone and 5,6-epoxy-5,6-dihydro-beta-ionone. A new direct access to enantiopure (R)- and (S)-alpha-ionone, J CHEM S P1, (3), 1999, pp. 271-278
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
3
Year of publication
1999
Pages
271 - 278
Database
ISI
SICI code
0300-922X(19990207):3<271:LSOTEF>2.0.ZU;2-2
Abstract
Stereoselective lipase-mediated esterifications of epoxy-alpha-ionol 5 and epoxy-beta-ionol 9 afforded suitable precursors of the enantiomers of the c orresponding oxidised derivatives epoxy-alpha-ionone 3 and epoxy-beta-ionon e 4. An interesting: development of this work is the easy conversion of ena ntiopure 3a and 3b into highly valuable enantiopure (S)- and (R)-ionone (1a and 1b) via a mild deoxygenation reaction.