HIGHLY ENANTIOSELECTIVE DIHYDROXYLATION OF OLEFINS BY OSMIUM-TETROXIDE WITH CHIRAL DIAMINES

Authors
NAKAJIMA M TOMIOKA K IITAKA Y KOGA K
Citation
M. Nakajima et al., HIGHLY ENANTIOSELECTIVE DIHYDROXYLATION OF OLEFINS BY OSMIUM-TETROXIDE WITH CHIRAL DIAMINES, Tetrahedron, 49(47), 1993, pp. 10793-10806
Citations number
51
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
47
Year of publication
1993
Pages
10793 - 10806
Database
ISI
SICI code
0040-4020(1993)49:47<10793:HEDOOB>2.0.ZU;2-C
Abstract
Enantioselective dihydroxylation of olefins by osmium tetroxide with c hiral diamines was examined. The hydroxylation employing 1 gave except ionally high optical yields in the production of diols from mono-, tra ns-di-, and trisubstituted olefins. Virtually complete asymmetric indu ction was observed in the reaction of trans-beta-methylstyrene. The st ereochemical outcome of the asymmetric reaction strongly suggested tha t the oxidation proceeded via organometallacycle 14.