SYNTHESIS OF AZASUGARS .2. ISOMERIZATION OF POLYHYDROXYLATED AZEPANES

Authors
POITOUT L LEMERRER Y DEPEZAY JC
Citation
L. Poitout et al., SYNTHESIS OF AZASUGARS .2. ISOMERIZATION OF POLYHYDROXYLATED AZEPANES, Tetrahedron letters, 37(10), 1996, pp. 1613-1616
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
10
Year of publication
1996
Pages
1613 - 1616
Database
ISI
SICI code
0040-4039(1996)37:10<1613:SOA.IO>2.0.ZU;2-4
Abstract
Isomerization of enantiopure C-2-symmetric 3,5-dihydroxyazepane deriva tives has been studied. The neighboring nitrogen participation occurs during mesylation to give a chloromethylpiperidine, whereas from the L -ido-azepane a chiral bridged morpholine structure (1R-(6endo, 7exo)-8 -oxa-3-azabicyclo[3.2.1] octane-6,7-diol) is obtained under Mitsunobu conditions.