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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 12
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Original Articles

A Convenient One-Step Catalytic Method for Obtaining Optically Active 2-Cyclopentenyl Benzoate from Cyclopentene

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Pages 1789-1794 | Received 24 Oct 1994, Published online: 23 Sep 2006

References

  • Muzart , J. and Aït Mohand , S. New. J. Chem. , in press., Metal-assisted oxidations, Part XLII. For part XLI, see
  • Latvia : Riga Technical University .
  • Spogliarich , R. , Vidotto , S. , Farnetti , E. , Graziani , M. and Verma Gulati , N. 1992 . Tetrahedron: Asymmetry , 3 : 1001 For connected studies, see
  • Fukazawa , T. and Hashimoto , T. 1993 . Tetrahedron: Asymmetry , 4 : 2323
  • Gupta , A. K. and Kazlauskas , R. J. 1993 . Tetrahedron: Asymmetry , 4 : 879
  • Asami , M. , Ishizaki , T. and Inoue , S. 1994 . Tetrahedron: Asymmetry , 5 : 793
  • Rawlinson , D. J. and Sosnovsky , G. 1972 . Synthesis , 1
  • Sheldon , R. A. and Kochi , J. K. 1981 . Metal-Catalyzed Oxidations of Organic Compounds , New York : Acad. Press .
  • Muzart , J. 1986 . Bull. Soc. Chim. Fr. , 65
  • Levina , A. and Muzart , J. Tetrahedron: Asymmetry , In press
  • Chemical yield was calculated on the amount of tert-butyl-peroxybenzoate introduced.
  • Levina , A. Unpublished results.
  • Optically pure (R)-2-cyclopenten-1-ol has [α]D = +116.6 (c= 0.64, CHCl3) from ref. 3b, while the value −137.9 (c = 1.1, CHCl3) has been previously attributed to (S)-2-cyclopenten-1-ol
  • Wahhab , A. , Tavares , D. F. and Rauk , A. 1990 . Can. J. Chem. , 68 : 1559 See also ref. 3a, 3c
  • Su , H. , Walder , L. , Zhang , Z. and Scheffold , R. 1988 . Helv. Chim. Acta , 71 : 1073
  • Sharpless , K. B. and Verhoeven , T. R. 1979 . Aldrichimica Acta , 12 : 63
  • (R)-proline is however much more expensive than the (S) isomer.
  • The color of the mixture changed during the reaction from dark blue through green to brown or red. During the work up, the color passed mainly into the water layer.

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