Versatile enantiopure tetrahydropyridine scaffold for piperidine library synthesis

ORGN 121

Richard H. Blaauw, richard.blaauw@chiralix.com and Peter N.M. Botman. Chiralix B.V, Toernooiveld 100, 6525 EC Nijmegen, Netherlands
The readily available enantiomerically pure tetrahydropiperidine scaffold 1 is a versatile building block for the synthesis of libraries of various types of substituted piperidines. Iodination, followed by Pd-catalyzed Suzuki and Sonogashira coupling reactions leads to the corresponding alkyl- and aryl-substituted pipecolic acid derivatives. Introduction of vinyl substituents provides 1,3-dienes that are well-suited for Diels-Alder reactions. Furthermore, oxidation of the enamide eventually gives rise to series of hydroxylated pipecolic acid derivatives.