title: Synthesis of chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octane derivatives.
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.
authors.affiliation: School of Chemistry, University of Hyderabad Central University, Hyderabad 500046, India.
authors.forename: Mariappan
authors.initials: M
authors.lastname: Periasamy
authors.affiliation: School of Chemistry, University of Hyderabad Central University, Hyderabad 500046, India.
authors.forename: Athukuri
authors.initials: A
authors.lastname: Edukondalu
authors.affiliation: School of Chemistry, University of Hyderabad Central University, Hyderabad 500046, India.
authors.forename: Polimera Obula
authors.initials: PO
authors.lastname: Reddy