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. 2018 Aug 3;20(15):4444-4448.
doi: 10.1021/acs.orglett.8b01723. Epub 2018 Jul 16.

Stereospecific Ring Opening and Cycloisomerization of Aziridines with Propargylamines: Synthesis of Functionalized Piperazines and Tetrahydropyrazines

Bijay Ketan Das  1 , Sourav Pradhan  1 , Tharmalingam Punniyamurthy  1
Affiliations

Stereospecific Ring Opening and Cycloisomerization of Aziridines with Propargylamines: Synthesis of Functionalized Piperazines and Tetrahydropyrazines

Bijay Ketan Das et al. Org Lett. .

Abstract

Stereospecific Cu-catalyzed nucleophilic ring opening of N-sulfonylaziridines with propargylamines and subsequent hydroamination afford piperazines, which leads to double-bond isomerization to furnish tetrahydropyrazines. Optically active aziridines can be cross-coupled with high enantiomeric purities (>98% ee).

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