Chemoselective asym. oxidn. of sulfides has been performed employing inexpensive and easily accessible camphor-derived hydroperoxides in the presence of catalytic loadings of Ti(Oi-Pr)4 (20 mol %) and MS 4 A. Aryl Me sulfoxides of both abs. configurations can be obtained with enantioselectivities of up to 51%. For the first time, the kinetic resoln. of racemic sulfoxides, mediated by the same chiral oxidative system has been found to be stereodivergent with respect to the sulfoxidn. step. At the end of the oxidns., camphor-derived alcs. were isolated by silica gel chromatog. and recycled for the synthesis of the hydroperoxides, thus providing a valuable chiral resource saving protocol.
Enantioselective sulfoxidation mediated by renewable camphor-derived hydroperoxides
LATTANZI, Alessandra;IANNECE, Patrizia;SCETTRI, Arrigo
2004-01-01
Abstract
Chemoselective asym. oxidn. of sulfides has been performed employing inexpensive and easily accessible camphor-derived hydroperoxides in the presence of catalytic loadings of Ti(Oi-Pr)4 (20 mol %) and MS 4 A. Aryl Me sulfoxides of both abs. configurations can be obtained with enantioselectivities of up to 51%. For the first time, the kinetic resoln. of racemic sulfoxides, mediated by the same chiral oxidative system has been found to be stereodivergent with respect to the sulfoxidn. step. At the end of the oxidns., camphor-derived alcs. were isolated by silica gel chromatog. and recycled for the synthesis of the hydroperoxides, thus providing a valuable chiral resource saving protocol.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
