SYNTHESIS OF ENANTIOPURE CYCLOPENTITOLS AND AMINOCYCLOPENTITOLS MEDIATED BY OXYSELENENYLATION OF CYCLOPENTENE WITH (R,R)-HYDROBENZOIN

Authors
KIM KS PARK JI DING PY
Citation
Ks. Kim et al., SYNTHESIS OF ENANTIOPURE CYCLOPENTITOLS AND AMINOCYCLOPENTITOLS MEDIATED BY OXYSELENENYLATION OF CYCLOPENTENE WITH (R,R)-HYDROBENZOIN, Tetrahedron letters, 39(36), 1998, pp. 6471-6474
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
36
Year of publication
1998
Pages
6471 - 6474
Database
ISI
SICI code
0040-4039(1998)39:36<6471:SOECAA>2.0.ZU;2-S
Abstract
Oxyselenenylation of cyclopentene with (R,R)-hydrobenzoin and subseque nt oxidation-elimination of the resulting oxyselenide 1 afforded olefi n 2. Intramolecular oxyselenenylation of 2 occurred in a completely re gio- and stereoselective manner to give oxyselenide 3. Further transfo rmation of 2 and 3 provided enatiomerically pure cyclopentanetriol 7, cyclopentanetetrol 9, aminocyclopentitol 15, and cyclopentitol 19. (C) 1998 Elsevier Science Ltd. All rights reserved.