Synlett 1991; 1991(1): 60-62
DOI: 10.1055/s-1991-20630
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Optically Active Cyclopentanones from Chiral Malonates: A Versatile Approach to (+)-α-and (-)-β-Cuparenones

Antoine Fadel* , Jean-Louis Canet, Jacques Salaün
  • *Laboratoire des Carbocycles, associé au C.N.R.S., Institut de Chimie Moléculaire d'Orsay, Bât. 420, Université de Paris-Sud, F-91405 Orsay, France
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Publication History

Publication Date:
07 March 2002 (online)

Optically active α- and β-cuparenones (2,2,3-trimethyl-3 p-tolylcyclopentanone and 3,3,4-trimethyl-4-p-tolylcyclopentanone) are obtained from chiral malonate (+)-3 (methyl hydrogen (R)-methyl(p-tolyl)malonate) via ketoaldehyde (-)-15 (2-methyl-4-oxo-2-p-tolylpentanal) and succinate (+)-7 dimethyl (S)-2-methyl-2-p-tolylsuccinate), respectively. Furthermore, syntheses of the new chiral γ-butyrolactones (+)-12 and (+)-17 are also reported.

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