Synthesis of enantiopure cyclopentitols and aminocyclopentitols mediated by oxyselenenylation of cyclopentene with (R,R)-hydrobenzoin

Article abstract of DOI:10.1016/S0040-4039(98)01377-X

Oxyselenenylation of cyclopentene with (R,R)-hydrobenzoin and subsequent oxidation-elimination of the resulting oxyselenide 1 afforded olefin 2. Intramolecular oxyselenenylation of 2 occurred in a completely regio- and stereoselective manner to give oxyselenide 3. Further transformation of 2 and 3 provided enatiomerically pure cyclopentanetriol 7, cyclopentanetetrol 9, aminocyclopentitol 15, and cyclopentitol 19.