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Asymmetric Cyclization of α-Silyl Esters to Give Functionalized Hydrindanones


  • This work was supported by the Fonds der Chemischen Industrie (doctoral stipend for T. B.). We thank the Schering AG for their financial support and donation of chemicals.


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Desilylations can trigger the intramolecular aldol reaction of alicyclic tricarbonyl compounds. Ester enolates are formed selectively and cyclize to give functionalized hydrindanones [Eq. (a); R1 = (−)-menthyl, (−)- and (+)-phenylmenthyl; SiR3 [DOUBLE BOND] SiMe3, SiPh2Me]. The cyclization products are extremely important and useful synthetic building blocks for the synthesis of steroids.

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