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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Preparation of enantiopure 1-azabicyclo[3.2.2]nonanes functionalized at carbon C3, from cinchonine and cinchonidine. stereoselective solvolysis and an easily enolizable ketone.

Solvolysis of C9 mesylated cinchonidine 1-OMs and cinchonine 2-OMs in solvent MeOH, EtOH, and CF(3)CH(2)OH affords ring-expanded 1-azabicyclo[3.2.2]nonanes oxygenated at carbon C3 ("second Cinchona rearrangement"). The newly introduced substituents at C3 and the neighboring quinolyl group Q' at C2 adopt quasiequatorial positions. The derived 1-azabicyclo[3.2.2]nonan-3-ones 5 and 6 are easily equilibrated. On contact with MeOD uptake of deuterium takes place at room temperature.[1]

References

  1. Preparation of enantiopure 1-azabicyclo[3.2.2]nonanes functionalized at carbon C3, from cinchonine and cinchonidine. stereoselective solvolysis and an easily enolizable ketone. Röper, S., Franz, M.H., Wartchow, R., Hoffmann, H.M. J. Org. Chem. (2003) [Pubmed]
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