A mechanistically guided design leads to the synthesis of an efficient and practical new reagent for the highly enantioselective, catalytic dihydroxylation of olefins.
[structure: see text] The catalytic asymmetric dihydroxylation of olefins has been accomplished with high enantioselectivities using a proline-based catalyst. The pre-transition-state assembly for styrene is shown.
Huang
Jinkun
J
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Corey
E J
EJ
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006900:Hydroxylation; D007202:Indicators and Reagents / Q000138:chemical synthesis; D008024:Ligands; D015394:Molecular Structure; D009993:Osmium Tetroxide / Q000737:chemistry; D016877:Oxidants / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives; D013237:Stereoisomerism; D020058:Styrene / Q000737:chemistry; D013997:Time Factors
D000475:Alkenes; D007202:Indicators and Reagents; D008024:Ligands; D016877:Oxidants; D020058:Styrene; D011392:Proline; D009993:Osmium Tetroxide