anti Selective dihydroxylation by the ketimine derivatives of the allylic amine in monosubstituted olefins

Transformation of the allylic amine of monosubstituted olefins into the aryl ketimine derivatives resulted in consistent higher anti diastereofacial selectivity in the osmium-catalyzed dihydroxylation reactions, compared to the selectivities obtained from commonly used allylic amino derivatives such as N-acyl, N-Boc or N,N-dibenzyl. The anti selectivity ranged from 3:1 to 7:1 in dry THF and the best was observed with the 3,3′-difluorobenzophenone ketimine derivative. Application of the ketimine group is also reported with the substrates of biological importance.