Synthesis p. 818 - 820 (1989)
Update date:2022-08-04
Topics:
Kwiatkowski, Stefan
Syed, Ashfaq
Brock, Carolyn P.
Watt, David S.
Application of the Hajos-Parrish asymmetrically 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 >/= 95percent enantiomeric excess, as determined by 1H-NMR analysis using tris<3-heptafluoropropylhydroxymethylene)-(+)-camphorato>europium(III).
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