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Synthesis 1989; 1989(11): 818-820
DOI: 10.1055/s-1989-27400
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Enantioselective Synthesis of (-)-(7aS)-2,3,7,7a-Tetrahydro-7a- phenylthio-1H-indene-1,5(6H)-dione and (+)-(8aS)-3,4,8,8a-Tetrahydro-8a-phenylthio-1,6(2H,7H)-naphthalenedione

Stefan Kwiatkowski* , Ashfaq Syed, Carolyn P. Brock, David S. Watt
  • *Department of Chemistry, University of Kentucky, Lexington, KY 40 506, USA
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Publication Date:
02 May 2002 (online)

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Application of the Hajos-Parrish asymetrically biased aldol condensation to 2-(3-oxobutyl)-2-phenylthio-1,3-cyclopentanedione (5a) or 2-(3-oxobutyl) -2-phenylthio-1,3-cyclohexanedione (5b) using (R)-(+)-proline provided (-)-(7aS)-2,3,7,7a-tetrahydro-7a-phenylthio-1H-indene -1,5(6H)-dione (7a) and (+)-(8aS)-3,4,8,8a-tetrahydro-8a -phenylthio-1,6(2H,7H)-naphthalenedione (7b), respectively, in ≥ 95% enantiomeric excess, as determined by 1H-NMR analysis using tris[3-heptafluoropropylhydroxymethylene)-(+)-camphorato]europium(III).