Enantioselective vicinal hydroxylation of terminal and E-1,2-disubstituted olefins by a chiral complex of osmium tetraoxide. An effective controller system and a rational mechanistic model

The suprafacial hydroxylation of olefins by osmium tetraoxide, though a much used synthetic method, would become even more important if three conditions could be met: (1) modification to achieve high and predictable enantioselectivity and acyclic diastereoselectivity, (2) clarification of reaction m...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1989-12, Vol.111 (26), p.9243-9244
Main Authors: COREY, E. J, DASILVA JARDINE, P, VIRGIL, S, PO-WAI YUEN, CONNELL, R. D
Format: Article
Language:English
Subjects:
400200 > Inorganic, Organic, & Physical Chemistry
ALKENES
CALCULATION METHODS
CHALCOGENIDES
Chemical reactivity
Chemistry
DATA
DATA ANALYSIS
Exact sciences and technology
EXPERIMENTAL DATA
HYDROCARBONS
HYDROXYLATION
INFORMATION
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
MATERIALS SCIENCE
MEASURING INSTRUMENTS
MEASURING METHODS
NUMERICAL DATA
Organic chemistry
ORGANIC COMPOUNDS
OSMIUM COMPOUNDS
OSMIUM OXIDES
OXIDES
OXYGEN COMPOUNDS
Reactivity and mechanisms
REFRACTORY METAL COMPOUNDS
STEREOCHEMISTRY
TRANSITION ELEMENT COMPOUNDS 360204 > Ceramics, Cermets, & Refractories-- Physical Properties
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Summary:The suprafacial hydroxylation of olefins by osmium tetraoxide, though a much used synthetic method, would become even more important if three conditions could be met: (1) modification to achieve high and predictable enantioselectivity and acyclic diastereoselectivity, (2) clarification of reaction mechanism, and (3) facilitated recovery and recycling of osmium. This paper reports progress on all three fronts.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00208a025