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Dramatic enantioselectivity change in dihydroxylation of olefins with chiral amine-osmium tetroxide complex

✍ Scribed by Kiyoshi Tomioka; Makoto Nakajima; Kenji Koga

Book ID
104222137
Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
167 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

A slight structural modification of a chiral diamine 1 caused a dramatic change in a sense of enantioselectivity in dihydroxylation of olefns with chiral amine-osmium tetroxide complex.

Other possible mechanisq involving [3+2] cycloaddition of C=C with O=Os=O in any combinations do not lead to reasonable explanation for the change in a sense of enantioselectivity on the basis of steric ground.

πŸ“œ SIMILAR VOLUMES

Mechanistic aspects of asymmetric cis-di
Mechanistic aspects of asymmetric cis-dihydroxylation of olefins with osmium tetroxide employing a C2-symmetric chiral diamine
✍ Kiyoshi Tomioka; Makoto Nakajima; Yōichi Iitaka; Kenji Koga πŸ“‚ Article πŸ“… 1988 πŸ› Elsevier Science 🌐 French βš– 302 KB

Stereochemical consideration of the eficient enantioselective oxidation of trans-stilbene employing a C2-symmetric chiral diamine (5) strongly indicates an organometallocycle (2) as a possible intermediate in the oxidation of olefns with osmium tetroxide.