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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 8
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Original Articles

Studies Toward the Diastereoselective Reduction of 2-Alkoxycarbonyl-2-allyl-cyclopentanone Derivatives with Boron Hydrides

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Pages 1133-1144 | Received 11 Oct 1994, Published online: 23 Sep 2006

References

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  • Garcia , V. L. and Barreiro , E. J. 1985 . 9th International Symposium Synthesis in Organic Chemistry , England : University of Oxford .
  • Garcia , V. L. and Barreiro , E. J. 1985 . Abstracts of 10 th International Congress of Heterocyclic Chemistry , P8 – 238 . Canada : University of Waterloo .
  • Fraga , C. A. M. PhD Thesis , in preparation
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  • Fujii , H. , Oshima , K. and Utimoto , K. 1991 . Tetrahedron Letters , 32 : 6147 – 50 . The diastereoselective reduction of acyclic 3-keto esters is well discussed in
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  • The GC was performed in a OV-225 (50% cyanopropylmethyl, 50% phenylmethyl polysiloxane) capillary column (20 m × 0.25 mm) at 140°C
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  • Preite , M. D. 1994 . Quimica Nova , 17 : 137 – 151 .
  • The diastereomeric 2-allyl-2-alkoxycarbonyl-cyclopentanol mixture (2-3) was refluxed with MCPBA in CH2C12 for 3 h or 16 h1 affording the 2-oxabicyclo-[3.3.0]-octane system (la) or the functionalized trans-2-oxabicyclo-[4.3.0]-nonane system homologue of (1), respectively, that showed a characteristic pattern at δ 4.45–4.65 and δ 5.00 ppm, respectively, in the 1H NMR spectra allowed us to distinguish about which diastereomeric alcohol source (2 or 3) is predominant.
  • Lipkowitz , K. B. and Peterson , M. A. 1993 . Chem. Rev. , 93 : 2463 – 2486 . For a review see:
  • Sant'Anna , C. M. , Fraga , C. A. M. and Barreiro , E. J. unpublished results.
  • Fujii , H. , Oshima , K. and Utimoto , K. 1992 . Chem. Letters , : 967 – 70 .
  • Pinkney , P. S. 1943 . Org. Synth. Coll. , Vol. II : 116

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