ABSOLUTE-CONFIGURATION OF 3-SUBSTITUTED 1-AZABICYCLO[2.2.1]HEPTANES

Authors
BOELSTERLI J EGGNAUER U POMBOVILLAR E WEBER HP WALKINSHAW M GOULD RO
Citation
J. Boelsterli et al., ABSOLUTE-CONFIGURATION OF 3-SUBSTITUTED 1-AZABICYCLO[2.2.1]HEPTANES, Helvetica Chimica Acta, 75(2), 1992, pp. 507-512
Citations number
32
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
75
Issue
2
Year of publication
1992
Pages
507 - 512
Database
ISI
SICI code
0018-019X(1992)75:2<507:AO31>2.0.ZU;2-U
Abstract
The 1-azabicyclo[2.2.1]heptan-3-exo-ol (2) was resolved by fractional crystallisation of its hydrogen tartrate salts. The enantiomers (+)- a nd (-)-2 were oxidised to the ketones (-)-4 and (+)-4, respectively (S cheme). CD spectroscopy suggested that (-)-4 possesses the (1R,4S)-con figuration. This absolute configuration was confirmed by single-crysta l X-ray diffraction of the derivative 1,3-dithian-2-ylidene)-1-azabicy clo[2.2.1]-heptane ((+)-5).