Synthesis of chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octane derivatives

The Journal of Organic Chemistry
Mariappan PeriasamyPolimera Obula Reddy

Abstract

Racemic 2,3-diaryl-1,4-diazabicyclo[2.2.2]octane (DABCO) derivatives are synthesized from the readily accessible piperazines in 50-64% yield by cyclization using ethylene bromide, triethylamine, and KI at 80 °C. The enantiomerically enriched 2,3-diphenylpiperazine and the 2,3-bis(1-naphthyl)piperazine derivatives are prepared by a resolution method using commercially available optically active acids, yielding the corresponding DABCO derivatives in 51-64% yield with up to 99% ee. This mild cyclization can also be applied to enantiopure camphanyldiamine derivatives, and the products are obtained in 72-86% yields.

References

Aug 14, 2003·Chemical Reviews·Stefan FranceThomas Lectka
Apr 22, 2006·The Journal of Organic Chemistry·Pothiappan Vairaprakash, Mariappan Periasamy
Apr 3, 2007·Angewandte Chemie·Géraldine MassonJieping Zhu
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Jul 23, 2013·Angewandte Chemie·Jamie R WolstenhulmeVéronique Gouverneur
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