Reliable chiral transfer through thermodynamic equilibrium of the intramolecular Meerwein–Ponndorf–Verley reduction and Oppenauer oxidation

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Morifumi Fujita, Yoshihiro Takarada, Takashi Sugimura and Akira Tai


Abstract

Forward and reverse hydride transfer with rigorous diastereodifferentiation is attained using intramolecular Meerwein–Ponndorf–Verley reduction and Oppenauer oxidation of a 2-acetylphenyl ether containing an optically active 3-hydroxy-1-methylbutyl group.


References

  1. For recent review, see C. E. de Graauw, J. A. Peters, H. van Bekkum and J. Huskens, Synthesis, 1994, 1007 Search PubMed.
  2. K. Nishide, Y. Shigeta, K. Obata and M. Node, J. Am. Chem. Soc., 1996, 118, 13 103 CrossRef CAS.
  3. G. A. Molander and J. A. Mckie, J. Am. Chem. Soc., 1993, 115, 5821 CrossRef CAS.
  4. K. Ishihara, N. Hanaki and H. Yamamoto, Synlett., 1993, 127 CrossRef CAS; K. Ishihara, N. Hanaki and H. Yamamoto, J. Am. Chem. Soc., 1993, 115, 10 695 CrossRef CAS; K. Ishihara, N. Hanaki and H. Yamamoto, J. Am. Chem. Soc., 1991, 113, 7074 CrossRef CAS.
  5. W. S. Zhou, X. M. Zhou and Y. Ni, Acta Chim. Sinica, 1984, 42, 706 Search PubMed; W. S. Zhou, Z. Q. Wang, H. Zhang, R. Y. Fei and Z. P. Zhuang, Acta Chim. Sinica, 1985, 43, 168 Search PubMed.
  6. T. Sugimura, J. Synth. Org. Chem. Jpn., 1997, 55, 517 Search PubMed.
  7. J. B. Pedley, R. D. Naylor and S. P. Kirby, Thermochemical Data of Organic Compounds, Chapman and Hall, London, 1986 Search PubMed.
  8. T. Sugimura, H. Yamada, S. Inoue and A. Tai, Tetrahedron: Asymmetry, 1997, 8, 649 CrossRef CAS.
  9. T. Hayashi, Y. Matsumoto and Y. Ito, Tetrahedron: Asymmetry, 1991, 2, 601 CrossRef CAS; P. V. Ramachandran, B. Gong and H. C. Brown, Tetrahedron Lett., 1994, 35, 2141 CrossRef CAS.
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