New enantiopure 7-azanorbornane β-substituted prolines by SN2 displacements at the Cγ of the side chain

Continuing our work on building new beta-substituted prolines in en antiomerically pure form as new surrogates to be incorporated into model peptides, we describe functional group conversions and carbon-carbon bond forming reactions by S(N)2 displacements at the gamma-position of the alpha-amino acid side chain of an azanorbornane derivative. This work extends efforts on the elaboration of the side arm at carbon C2 of the 7-azabicyclo[2.2.1]heptane core. (C) 2005 Elsevier Ltd. All rights reserved.