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
On the dihydroxylation of cyclic allylic alcohols
โ Scribed by Timothy J. Donohoe; Rina Garg; Peter R. Moore
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 240 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
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-hommll
A highly diastereoselective dihydroxylation protocol has been developed for acyclic allylic alcohol derivatives leading to triol derivatives with diastereoselectivity reversed to the classical osmylation (anti-Kishi). Selectivities ate acceptable for E-allylic derivatives 1, and high for those deriv