Substrate directed diastereoselective hydroformylation of acyclic homomethallylic alcohols

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Bernhard Breit


Abstract

Diastereoselective hydroformylation of acyclic homomethallylic alcohols with the aid of a catalyst directing group is achieved and the stereochemical outcome of this reaction is rationalized by analysing the preferred substrate conformation in solution.


References

  1. M. Sakai, S. Mano, K. Nozaki and H. Takaya, J. Am. Chem. Soc., 1993, 115, 7033 CrossRef CAS; B. M. Trost, Acc. Chem. Res., 1996, 29, 355 CrossRef CAS; Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993 Search PubMed.
  2. A. H. Hoveyda, D. A. Evans and G. C. Fu, Chem. Rev., 1993, 93, 1307 CrossRef CAS.
  3. A. H. Hoveyda and Z. Xu, J. Am. Chem. Soc., 1991, 113, 5079 CrossRef CAS; A. H. Hoveyda, Z. Xu, J. P. Morken and A. F. Houri, J. Am. Chem. Soc., 1991, 113, 8950 CrossRef CAS as well as refs. 4 and 5.
  4. S. D. Burke and J. E. Cobb, Tetrahedron Lett., 1986, 27, 4237 CrossRef CAS; W. R. Jackson, P. Perlmutter and E. E. Tasdelen, J. Chem. Soc., Chem. Commun., 1990, 763 RSC; M. T. Didiuk, J. P. Morken and A. H. Hoveyda, J. Am. Chem. Soc., 1995, 117, 7273 CrossRef CAS.
  5. B. Breit, Angew. Chem., 1996, 108, 3021; Angew. Chem., Int. Ed. Engl., 1996, 35, 2835 Search PubMed.
  6. H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto and T. Taga, J. Am. Chem. Soc., 1987, 109, 5031 CrossRef CAS; T. Kino, H. Hatanaka, M. Hashimoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki and H. Imanaka, J. Antibiot., 1987, 40, 1249 CAS Aplyronine A/B/C: K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto and M. Arakawa, J. Am. Chem. Soc., 1993, 115, 11 020 Search PubMed Palytoxin: J. K. Cha, W. J. Christ, J. M. Finan, H. Fujioka, Y. Kishi, L. L. Klein, S. S. Ko, J. Leder, W. W. McWhorter Jr., K.-P. Pfaff, M. Yonaga, D. Uemura and Y. Hirata, J. Am. Chem. Soc., 1982, 104, 7369 CrossRef CAS Herbimycin: S. Omura, A. Nakagawa and N. Sadakane, Tetrahedron Lett., 1979, 4323 Search PubMed side chain of Maitotoxin: M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana and T. Yasumoto, Angew. Chem., 1996, 108, 1782 CrossRef CAS AAL-Toxin TA1: A. T. Bottini and D. G. Gilchrist, Tetrahedron Lett., 1981, 22, 2719 Search PubMed Fumonisin B1: S. C. Bezuidenhout, W. C. A. Gelderblom, C. P. Gorst-Allman, R. M. Horak, W. F. O. Marasas, G. Spiteller and R. Vleggaar, J. Chem. Soc., Chem. Commun., 1988, 743 CrossRef CAS.
  7. T. Imai and S. Nishida, Synthesis, 1993, 395 CrossRef CAS.
  8. G. Höfle, W. Steglich and H. Vorbrüggen, Angew. Chem., 1978, 90, 602 CrossRef; Angew. Chem., Int. Ed. Engl., 1978, 17, 569 Search PubMed.
  9. R. W. Hoffmann, Chem. Rev., 1989, 89, 1841 CrossRef CAS; R. W. Hoffmann, Angew. Chem., 1992, 104, 1147 CAS; Angew. Chem., Int. Ed. Engl., 1992, 31, 1124 Search PubMed; R. Göttlich, C. Kahrs, J. Krüger and R. W. Hoffmann, Chem. Commun., 1997, 247 Search PubMed.
  10. B. Bardili, H. Marschall-Weyerstahl and P. Weyerstahl, Liebigs Ann. Chem., 1985, 275 Search PubMed.
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