The first catalytic
asymmetric cyclopropanation of diazo oxime
ethers with olefins was developed. In the presence of a Ru(II)-Pheox
catalyst, various optically active cyclopropyl oxime derivatives were
obtained in high yields (up to 99%) with high enantioselectivities
(up to 98% ee). Furthermore, optically active cyclopropyl oxime ethers
could be successfully converted into the corresponding cyclopropyl
methylamine derivatives via metal hydride and Grignard reagent mediated
Beckmann rearrangement, which are potential candidates for the assessment
of biological and pharmaceutical activities.
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