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The asymmetric dihydroxylation of cis-allylic and homoallylic alcohols

โœ Scribed by Michael S. VanNieuwenhze; K.Barry Sharpless

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
277 KB
Volume
35
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The asymmetric dihydroxylation of several ck allylic alcohols is reported. The reactions proceed with moderate to good enantioselectivity. The enhanced enantioselection observed relatitie to other cis-olefin classes is believed to be dependent on the presence of the free hydroxyl group. A cis-hommllylic alcohol also gave a useful level of enantiose1ection in the AD.

๐Ÿ“œ SIMILAR VOLUMES

The directed dihydroxylation of allylic
The directed dihydroxylation of allylic alcohols
โœ Timothy J. Donohoe; Peter R. Moore; Michael J. Waring; Nicholas J. Newcombe ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 254 KB

The preparation and dihydroxylation of a series of polyenes and cyclic ailylic alcohols using the TMEDA/osmium tetroxide mixture is reported. Remarkably, these reagents lead to high levels of regiochemical and stereochemical control as the oxidant hydrogen-bonds to the allylic alcohol group. A mecha