✦ LIBER ✦

On the stereochemistry of osmium tetraoxide oxidations of allylic systems used in the synthesis of higher-carbon sugars

✍ Scribed by John S. Brimacombe; Abul K.M.S. Kabir

Publisher: Elsevier Science
Year: 1988
Tongue: English
Weight: 613 KB
Volume: 179
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(88)84106-5

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✦ Synopsis

The stereochemistry of the major osmylation products of carbohydrate-based allylic alcohols can usually be predicted by application of Kishi's empirical rule. In particular, the addition of 0~0, can be formulated as taking place in the more abundant conformation on the surface anti to a pyranose or furanose ring-oxygen atom located at a stereocentre adjacent to the olefinic linkage. Exceptions to Kishi's empirical rule for osmylation are sometimes encountered with conjugated carbonyl compounds.

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