Enatio- and diastereoselective construction of 4, 9-dimethylspiro[4.4]nonane-2, 7-dione using Rh-catalyzed asymmetric cyclization

  • Tanaka M
  • Takahashi M
  • Sakamoto E
 et al. 
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Abstract

Asymmetric cyclization using Rh-complexes was applied to the synthesis of 4, 9-dimethylspiro[4.4]nonane-2, 7-diones. The spiro[4.4]nonane skeleton bearing a chiral quaternary carbon could be stepwisely constructed by using Rh-catalyzed cyclization twice. All diastereomers of the spirodiketone could be stereoselectively prepared from the identical starting material by the combination of a neutral Rh(PPh3)3Cl and a cationic Rh[BINAP]ClO4. The cyclization by the neutral Rh(PPh3)3Cl proceeded to give cis-3, 4-disubstituted cyclopentanones, while that by the cationic Rh[BINAP]ClO4proceeded to afford trans-3, 4-disubstituted cyclopentanones. Four spirodiketones of six stereoisomers could be prepared in optically active form, and the relationship between the stereochemistry of the spirodiketones and the Rh-complex was discussed based on the plausible acyl-hydride Rh-complexes. © 2001 Elsevier Science Ltd.

Author-supplied keywords

  • Asymmetric reactions
  • Cyclization
  • Rhodium
  • Spiro compounds

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Authors

  • Masakazu Tanaka

  • Miyuki Takahashi

  • Eishi Sakamoto

  • Masanori Imai

  • Akiko Matsui

  • Masakazu Fujio

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