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Influence of enolate geometry and structure on the stereochemistry of the asymmetric oxidation of prochiral ketone enolates to optically active α-hydroxy ketones

✍ Scribed by Franklin A. Davis; Aurelia C. Sheppard; G.Sankar Lal

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
309 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

The sfereoselectiviry for the asymmetric oxidation of enolafes to opfica//y active a-hydroxy ketones using (+)-( camphoryisulfonyi)oxaziridine is dependent on the enoiate substitution pattern, the solution structure of the enoiate and to a lesser extent the enoiate geometry Optically active a-hydroxy carbonyl compounds 4 are key intermediates in the enantioselective synthesis of natural products and a common feature of many biologically important molecules. 1 A convenient route to ihls Important structural array is the direct oxidation of homochiral enolates with N-sutfonyloxaziridine 5, an aprotic oxidizing reagent.1b.d Recently we introduced methodology for the asymmetric oxidation of prochiral enolates to optically active n-hydroxy carbonyl compounds using (+) and f-)-(camphorylsulfonyl)oxaziridines 6 (50.96% ee).2 Since the configuration of the

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