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Synthesis 1999; 1999(2): 258-263
DOI: 10.1055/s-1999-3393
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Methylenation and Oxidation of Chiral Non-Racemic 2-Piperidones: Reactivity of a New 3-Oxolactam

Pilar Forns* , Montserrat Fernández, Anna Diez, Mario Rubiralta, Marie Pierre Cherrier, Martine Bonin, Jean-Charles Quirion
  • *Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, 08028-Barcelona, Spain; Fax +34(93)4 02 18 96; E-mail: adiez@farmacia.far.ub.es
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Publication History

Publication Date:
31 December 1999 (online)

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The preparation of (R)-N-(2-hydroxy-1-phenylethyl)-3-methylenepiperidin-2-one (2) and (R)-N-(2-hydroxy-1-phenylethyl)piperidine-2,3-dione (3) from the (R)-phenylglycinol-derived lactam 1 is described. We have also studied the reactivity of 3-oxolactam 3, and a series of functionalized derivatives has been prepared.

3-methylenelactam - 3-oxolactam - 3-hydroxylactam - (R)-(-)-phenylglycinol - Wadsworth-Emmons Reaction