Jump to main content
Jump to site search

Issue 3, 2018
Previous Article Next Article

Efficient one-pot synthesis of enantiomerically pure N-protected-α-substituted piperazines from readily available α-amino acids

Author affiliations

Abstract

A new pathway towards enantiomerically pure 3-substituted piperazines, bearing a benzyl protecting group, has been developed in good overall yields (83–92%), starting from commercially available N-protected amino acids. The methodology represents an efficient and simple one-pot procedure, employing a synthetic sequence consisting of an Ugi-4 component reaction, a Boc-deprotection, an intramolecular cyclisation reaction and a final reduction (UDCR). From the benzyl protected precursors, the 2-substituted piperazines bearing a Boc-protecting group could consequently also be obtained via a simple protection and deprotection step of the corresponding piperazines. The practical utility of this methodology was demonstrated for chiral drug synthesis.

Graphical abstract: Efficient one-pot synthesis of enantiomerically pure N-protected-α-substituted piperazines from readily available α-amino acids

Back to tab navigation

Supplementary files

Publication details

The article was received on 19 Oct 2017, accepted on 27 Dec 2017 and first published on 03 Jan 2018


Article type: Letter
DOI: 10.1039/C7NJ04039C
Citation: New J. Chem., 2018,42, 1595-1599
  •   Request permissions

    Efficient one-pot synthesis of enantiomerically pure N-protected-α-substituted piperazines from readily available α-amino acids

    M. Jida and S. Ballet, New J. Chem., 2018, 42, 1595
    DOI: 10.1039/C7NJ04039C

Search articles by author

Spotlight

Advertisements