AN ACCESS TO ERYTHRO-DIOLS VIA SHARPLESSS ASYMMETRIC DIHYDROXYLATION REACTION

A method has been developed to access erythro-2,3-diols via Sharpless' s asymmetric dihydroxylation reaction. Thus, a TBDMS-protected (E)-all ylic alcohol is dihydroxylated and the resulting threo-2,3-diol is con verted to the cyclic sulfate. Upon desilylation, this compound undergo es a Payne-type rearrangement. Nucleophilic epoxide-opening then provi des an erythro-2,3-diol. The conversions from the cyclic sulfate to th e diol product are performed in a single reaction vessel. Due to the i rreversible nature of the Payne-type rearrangement, this process is ea sy to perform and completely regioselective independent of the substra te structures. Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, N--(3), (OAc)-O- -, (CN)-C--, halides as well as carbon nucleophiles and hydride.