Selective oxidation of penicillin derivatives to penicillin (1R) and (1S)-sulfoxides using dimethyldioxirane

DANELON, GERARDO O.; MATA, ERNESTO G.; MASCARETTI, ORESTE A.

TETRAHEDRON LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Año: 1993 vol. 34 p. 7877 - 7880

0040-4039

We describe a convenient procedure for preparing (1R)-6,6-dihalo-, 6β-halo-penicillanates, 6,6-dihalopenam derivatives and (1S)-6-α-halopenicillanates sulfoxides by dimethyldioxirane asymmetric oxidation of the corresponding penicillanates and penam derivatives. This method is characterized by mild reactions conditions, short reaction times, excellent selectivity, very high yield, ease of reaction workup and complete avoidance of overoxidation products