CONVERSION OF ONE ENANTIOMER OF THE CARBOCYCLIC NUCLEOSIDE SYNTHON 2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONE INTO THE OTHER

Authors
PALMER CF MCCAGUE R
Citation
Cf. Palmer et R. Mccague, CONVERSION OF ONE ENANTIOMER OF THE CARBOCYCLIC NUCLEOSIDE SYNTHON 2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONE INTO THE OTHER, Journal of the Chemical Society. Perkin transactions. I, (10), 1995, pp. 1201-1203
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
10
Year of publication
1995
Pages
1201 - 1203
Database
ISI
SICI code
0300-922X(1995):10<1201:COOEOT>2.0.ZU;2-#
Abstract
The lactam synthon 2-azabicyclo[2.2.1]hept-5-en-3-one was converted in to its enantiomer by a 5-step sequence incorporating a skeletal rearra ngement mediated by anchimeric assistance of the nitrogen atom; the ro ute proceeded via a tosylate intermediate prone to racemization.