J. Boelsterli, U. Eggnauer, E. Pombo-Villar
Mar 18, 1992
Citations
0
Influential Citations
12
Citations
Journal
Helvetica Chimica Acta
Abstract
The l-azabicyclo[2.2.1]heptan-3-exo-ol (2) was resolved by fractional crystallisation of its hydrogen tartrate salts. The enantiomers (+)- and (−)-2 were oxidised to the ketones (−)-4 and (+)-4, respectively (Scheme). CD spectroscopy suggested that (−)-4 possesses the (1R,4S)-configuration. This absolute configuration was confirmed by single-crystal X-ray diffraction of the derivative (+)-(1R,4R)-3-(1,3-dithian-2-ylidene)-1-azabicyclo [2.2.1]-heptane ((+)-5).