An efficient synthetic approach for N–C bond formation from (S)-amino acids: an easy access to cis-2,5-disubstituted chiral piperazines?

RSC Advances Pub Date: 2013-07-29 DOI: 10.1039/C3RA42309C

Abstract

An efficient synthetic strategy is described for the construction of amino acids derived enantiomerically pure cis-2,5-disubstituted chiral piperazines. Cu-catalyzed spontaneous regioselective ring opening and ring closing of non-activated N-tosyl aziridines as well as Pd-mediated N–C bond formation from N-tosyl halogenated amino-derivatives are the key steps for accessing disubstituted piperazines.

Graphical abstract: An efficient synthetic approach for N–C bond formation from (S)-amino acids: an easy access to cis-2,5-disubstituted chiral piperazines
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