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Absolute Configuration of 3-Substituted 1-Azabicyclo[2.2.1]heptanes

✍ Scribed by Jakob Boelsterli; Ursula Eggnauer; Esteban Pombo-Villar; Hans-Peter Weber; Malcolm Walkinshaw; Robert O. Gould

Publisher
John Wiley and Sons
Year
1992
Tongue
German
Weight
396 KB
Volume
75
Category
Article
ISSN
0018-019X

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✦ Synopsis

The l-azabicyclo[2.2. I]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 (IR,4S)-configuration. This absolute configuration was confirmed by single-crystal X-ray diffraction of the derivative (+)-(I R,4R)-3-( 1,3-dithian-2-ylidene)-1 -azabicyclo[2.2. I]heptane ((+)-5).

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