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Synlett 1991; 1991(12): 863-864
DOI: 10.1055/s-1991-20903
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An Asymmetric Synthesis of 7a-Alkyl-2,4,5,6,7,7a-hexahydro-1H-inden-2-one

A. I. Meyers* , Lawrence B. Snyder
  • *Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA
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Publikationsdatum:
07. März 2002 (online)

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A route to the title compounds in > 99 % enantiomeric excess was achieved from sequential diastereoselective alkylations of chiral, non-racemic bicyclic lactams 5 (3-alkyl-7a-methyl-5-oxo-hexahydropyrrolo[2,1-b]oxazoles). An intramolecular addition of the organolithium derivative 9 [3,6-dialkyl-6-(4-lithiobutyl)-7a-methyl-5-oxo-hexahydropyrrolo[2,1-b]oxazoles], gave, after hydrolysis, the diketone 11 [2-alkyl-2-(2-oxopropyl)cyclohexanone], which was cyclized to the optically pure title compounds 12-14.