Issue 3, 2018

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

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

Supplementary files

Article information

Article type
Letter
Submitted
19 Oct 2017
Accepted
27 Dec 2017
First published
03 Jan 2018

New J. Chem., 2018,42, 1595-1599

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

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