An unprecedented entry to 5,6-dihydroxy-2-azabicyclo[2.2.1]heptan-3-one

Authors
Palmer, CF Bannister, RM McCague, R
Citation
Cf. Palmer et al., An unprecedented entry to 5,6-dihydroxy-2-azabicyclo[2.2.1]heptan-3-one, TETRAHEDR L, 40(33), 1999, pp. 6109-6112
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
33
Year of publication
1999
Pages
6109 - 6112
Database
ISI
SICI code
0040-4039(19990813)40:33<6109:AUET5>2.0.ZU;2-G
Abstract
A catecholborane mediated reaction of the lactam epoxide unexpectedly gave the cis-diol a useful intermediate for adenosine agonists. The origin of th is reaction is postulated to arise from the formation of a boronic anhydrid e which is transferred to the electron deficient C-6 via transannular attac k by the amide nitrogen. (C) 1999 Elsevier Science Ltd. All rights reserved .