Anti-Kishi selective dihydroxylation of allylic alcohol derivatives
โ Scribed by Oili A. Kallatsa; Ari M.P. Koskinen
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 197 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
โฆ Synopsis
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 derived from Z-derivatives 4.
๐ SIMILAR VOLUMES
Transformation of the allylic amine of monosubstituted olefins into the aryl ketimine derivatives resulted in consistent higher anti diastereofacial selectivity in the osmium-catalyzed dihydroxylation reactions, compared to the selectivities obtained from commonly used allylic amino derivatives such
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