A Simple Method of Synthesis of (±)-2,3-Diarylpiperazines and a Novel Method of Resolution of (±)-2,3-Diphenylpiperazine

Intramolecular reductive coupling of diimines in the presence of Zn/Ti(OiPr)2Cl2 gives the corresponding (±)-2,3-diarylpiperazines in 73−83% yields with dl/meso ratio >99%:99% ee via preparation of hydrogen-bonded salt aggregates using oxalic acid.

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Bibliographic Details
Published in:Journal of organic chemistry 2006-04, Vol.71 (9), p.3636-3638
Main Authors: Vairaprakash, Pothiappan, Periasamy, Mariappan
Format: Article
Language:English
Subjects:
Biphenyl Compounds - chemical synthesis
Biphenyl Compounds - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Oxidation-Reduction
Piperazines - chemical synthesis
Piperazines - chemistry
Preparations and properties
Stereoisomerism
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Description
Summary:Intramolecular reductive coupling of diimines in the presence of Zn/Ti(OiPr)2Cl2 gives the corresponding (±)-2,3-diarylpiperazines in 73−83% yields with dl/meso ratio >99%:99% ee via preparation of hydrogen-bonded salt aggregates using oxalic acid.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060083n