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

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...

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Bibliographic Details
Published in:Tetrahedron letters 1998, Vol.39 (36), p.6471-6474
Main Authors: Kim, Kwan Soo, Park, Jong, Ding, Pingyu
Format: Article
Language:English
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Summary: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. Oxyselenenylation of cyclopentene with ( R,R)-hydrobenzoin and subsequent transformation afforded cyclopentitols and aminocyclopentitols.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)01377-X