Abstract
Reaction of the acylated chloroenamine 7 with cyanide gave the endo-morpholino compound 11. The endo-morpholino configuration of 11 was established by subsequent ring closure reactions generating tricyclic derivatives 14, 16 and 17. LiAlH 4 reduction of 11 afforded aminoalcohol 12. The corresponding exo-morpholino isomer 20 could be obtained by LiAlH 4 reduction of exo-morpholino compound 19 which was accessible from N-tosylcarbamoylated chloroenamine 10 and cyanide. ΔGX values of 75.4–77.6 kJ/mol and 52.1 kJ/mol were determined for the morpholine dynamics in the two isomeric compounds 12 and 20, respectively. This demonstrates that 1H NMR spectroscopic determination of the dynamics of morpholine allows an assignment of the configuration even in the case of twofold substituted morpholinobicyclo[n.1.0]alkane derivatives.
Published Version
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