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

✍ Scribed by Joon Seok Oh; Doh Yeon Park; Bu Sop Song; Jae Gwang Bae; Seung Woong Yoon; Young Gyu Kim

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 160 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01654-4

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✦ Synopsis

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.

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