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ABSTRACT:
SUBMITTER: McCall WS
PROVIDER: S-EPMC2736366 | biostudies-literature | 2008 Dec
REPOSITORIES: biostudies-literature
McCall W Stephen WS Grillo Teresa Abad TA Comins Daniel L DL
The Journal of organic chemistry 20081201 24
Various multisubstituted piperidines containing a phenyl group at C-2 can be opened regio- and stereoselectively with cyanogen bromide. The ring-opened products contain useful cyanamide and benzylic bromide functional groups. The benzyl bromide can be cleanly reduced, or substituted with various nucleophiles via an S(N)2 process to add additional heteroatoms stereoselectively. This methodology is useful for the stereoselective synthesis of uniquely substituted alkylamine derivatives containing m ...[more]