ABSOLUTE-CONFIGURATION OF 2-SUBSTITUTED 2-AZABICYCLO[2.2.1]HEPT-5-ENES

Authors
POMBOVILLAR E BOELSTERLI J CID MM FRANCE J FUCHS B WALKINSHAW M WEBER HP
Citation
E. Pombovillar et al., ABSOLUTE-CONFIGURATION OF 2-SUBSTITUTED 2-AZABICYCLO[2.2.1]HEPT-5-ENES, Helvetica Chimica Acta, 76(3), 1993, pp. 1203-1215
Citations number
37
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
76
Issue
3
Year of publication
1993
Pages
1203 - 1215
Database
ISI
SICI code
0018-019X(1993)76:3<1203:AO22>2.0.ZU;2-Q
Abstract
The diastereoisomeric 2-substituted 2-azabicyclo[2.2.1]hept-5-enes 2-4 were prepared by aza-Diels-Alder reaction of cyclopentadiene with the corresponding methaniminium ions. Their relative configurations were deduced using H-1,H-1-ROESY experiments, and their absolute configurat ions were assigned from the crystal structure of the aziridinium deriv ative (-)-5. The absolute configuration of (+)-1, i.e. (1R), was assig ned by CD spectroscopy.