Asymmetric synthesis of 2, 6-methylated piperazines

JW Mickelson, KL Belonga…

Index: Mickelson, John W.; Belonga, Kenneth L.; Jacobsen, Jon E. Journal of Organic Chemistry, 1995 , vol. 60, # 13 p. 4177 - 4183

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Citation Number: 53

Abstract

The complete series of enantiopure 2, 6-methylated piperazines was synthesized utilizing two alternative reactions in the key bond-forming step. The dimethyl enantiomers,(2R, 6R)- and (2S, 6S)-2, 6-dimethylpiperazine (1, 2), were prepared using either a diastereoselective triflate alkylation or a novel intramolecular Mitsunobu reaction to set the required stereochemistry. The monomethyl derivatives,(R)-and (5')-tert-butyl 2-methyl-1- ...