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Synthesis 2001; 2001(2): 0235-0238
DOI: 10.1055/s-2001-10810
short paper
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Facile Deuteration of Chiral N,N′-Substituted Piperazines

Víctor Santes* , Elizabeth Gómez, Rosa Santillan, Norberto Farfán
  • *Departamento de Química, Centro de Investigación y de Estudios Avanzados del IPN, Apdo. Postal 14-740, 07000 México D. F., México; Fax +52(5)7477113; E-mail: jfarfan§mail.cinvestav.mx
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Publication Date:
31 December 2001 (online)

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The synthesis of four chiral N,N′-substituted piperazines stereoselectively labelled with deuterium atoms is described. The preparation was accomplished by reduction of norephedrine derived bisoxazolidines with LiAlD4 or BD3 · THF to afford 2,3-d 2-piperazine and 2,3-dimethyl-2,3-d 2-piperazine, while 2,2,3,3-d 4- and 2,2,3,3,5,6-d 6-piperazine were obtained from a strategically deuterated hydroxyethylenediamine precursor using the same route. In all cases, deuteration of bisoxazolidines proceeded with trans stereoselectivity.

bisoxazolidine - N,N′-substituted piperazine - amino alcohols - asymmetric synthesis - condensation - reductions