Synthesis of highly substituted enantiopure piperazines and ketopiperazines from vicinal N-sulfinyl diamines.

@article{Viso2006SynthesisOH,
  title={Synthesis of highly substituted enantiopure piperazines and ketopiperazines from vicinal N-sulfinyl diamines.},
  author={Alma Viso and Roberto Fern{\'a}ndez de la Pradilla and Aida Flores and Ana B. Garc{\'i}a and Mariola Tortosa and Mar{\'i}a L. L{\'o}pez-Rodr{\'i}guez},
  journal={The Journal of organic chemistry},
  year={2006},
  volume={71 4},
  pages={
          1442-8
        }
}
Enantiopure 1-benzyl-2,3-disubstituted piperazines (4) have been synthesized by treatment of N-sulfinyl-N-benzyldiamino alcohols (1) with diethyl oxalate and sodium methoxide followed by reduction with borane. Alternatively, the sulfinamido group was preserved by an N-acylation/cyclization protocol using alpha-chloroacetyl chloride that led to the synthesis of N-sulfinyl ketopiperazines (11). Ensuing elimination of the sulfinyl group with NaH produced imino ketopiperazines (9) that are suitably… 
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