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

Bijay Ketan Das; Sourav Pradhan; Tharmalingam Punniyamurthy

doi:10.1021/acs.orglett.8b01723

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

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

Authors

Bijay Ketan Das¹, Sourav Pradhan¹, Tharmalingam Punniyamurthy¹

Affiliation

¹ Department of Chemistry , Indian Institute of Technology Guwahati , Guwahati 781039 , India.

PMID: 30011217
DOI: 10.1021/acs.orglett.8b01723

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).

Publication types

Research Support, Non-U.S. Gov't