ENANTIOSELECTIVE SYNTHESIS OF GAMMA-LACTONE AND DELTA-LACTONE

Authors
RUANO JLG FUERTE A MAESTRO MC
Citation
Jlg. Ruano et al., ENANTIOSELECTIVE SYNTHESIS OF GAMMA-LACTONE AND DELTA-LACTONE, Tetrahedron : asymmetry, 5(8), 1994, pp. 1443-1446
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
8
Year of publication
1994
Pages
1443 - 1446
Database
ISI
SICI code
0957-4166(1994)5:8<1443:ESOGAD>2.0.ZU;2-C
Abstract
The synthesis of enantiomerically pure sulfinyl oxoacids HO2CCH2(CH2)( n)COCH(R)SOTol (n=1 and 2, R=H, CH3), and their stereoselective reduct ion with DIBAL catalysed by ZnBr2 are reported. The resulting hydroxys ulfoxides were cyclized in situ under acidic conditions yielding high yields of the corresponding gamma- and delta-lactones in high enantiom eric purity.