A NOVEL SYNTHESIS OF OPTICALLY-ACTIVE 4-BENZYLOXYCARBONYL-2-OXETANONES AND 4-ALKYLOXYCARBONYL-2-OXETANONES

Authors
CAMMAS S RENARD I BOUTAULT K GUERIN P
Citation
S. Cammas et al., A NOVEL SYNTHESIS OF OPTICALLY-ACTIVE 4-BENZYLOXYCARBONYL-2-OXETANONES AND 4-ALKYLOXYCARBONYL-2-OXETANONES, Tetrahedron : asymmetry, 4(8), 1993, pp. 1925-1930
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
4
Issue
8
Year of publication
1993
Pages
1925 - 1930
Database
ISI
SICI code
0957-4166(1993)4:8<1925:ANSOO4>2.0.ZU;2-L
Abstract
optically active 4-benzyloxy- and 4-alkyloxycarbonyl-2-oxetanones 1 ha ve been synthesized by intramolecular dehydration of optically active benzyl, methyl, methyl-2-butyl malates 6a,b,c. The reaction has been p erformed using triphenylphospbine and diisopropylazodicarboxylate as r eagents. Starting from L-(S)-malic acid as chiral synthon, (R)-beta-su bstituted beta-lactones 1 have been obtained with very high enantiomer ic excesses (> 98 %) resulting in inversion at the hydroxyl bearing ca rbon, due to the hydroxyl group activation. Compounds 1 are used as mo nomers in the preparation of poly (beta-malic acid) 3 derivatives.