Scandium triflate catalyzed in situ Prins-type cyclization: formations of 4-tetrahydropyranols and ethers

(Note: The full text of this document is currently only available in the PDF Version )

Wen-Chun Zhang, Ganapathy S. Viswanathan and Chao-Jun Li


Abstract

The reaction of aldehydes with homoallyl alcohols catalyzed by scandium triflate generates tetrahydropyran-4-ol and ethers in good yields.


References

  1. For reviews, see: E. Arundale and L. A. Mikeska, Chem. Rev., 1952, 51, 505 Search PubMed; D. R. Adams and S. P. Bhatnagar, Synthesis, 1977, 661 CrossRef CAS.
  2. K. C. Nicolaou and E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996 Search PubMed.
  3. The best known method in this regard is probably the hetero-Diels–Alder reaction with Danishefsky's diene; for examples, see: S. J. Danishefsky, W. H. Pearson and D. F. Harvey, J. Am. Chem. Soc., 1984, 106, 2456 Search PubMed; S. J. Danishefsky and C. J. Maring, J. Am. Chem. Soc., 1989, 111, 2193 CrossRef CAS.
  4. X. H. Yi, J. X. Haberman and C. J. Li, Synth. Commun., 1998, 28, 2999 CAS.
  5. J. Yang, G. S. Viswanathan and C. J. Li, Tetrahedron Lett., in the press Search PubMedSuch compounds were also accessible through TiCl4 and AlCl3 catalyzed allylsilane reactions of aldehydes cross–coupling between homoallyl alcohols and aldehydes, however, when both substituents are aromatic, the reaction provided no or a low yield of the product, see: Z. Y. Wei, J. S. Li, D. Wang and T. H. Chan, Tetrahedron Lett., 1987, 28, 3441 Search PubMed; F. Perron and K. F. Albizati, J. Org. Chem., 1987, 52, 4130 Search PubMed; Z. Y. Wei, D. Wang, J. S. Li and T. H. Chan, J. Org. Chem., 1989, 54, 5768 CrossRef CAS; L. Coppi, A. Ricci and M. Taddei, J. Org. Chem., 1988, 53, 913 CrossRef CAS Very recently, Rychnovsky and co-workers reported an interesting SnBr4-mediated segment-coupling Prins cyclization, see: S. D. Rychnovsky, Y. Hu and B. Ellsworth, Tetrahedron Lett., 1998, 39, 7271 CrossRef CAS.
  6. For a leading reference, see: S. Kobayashi and I. Hachiya, J. Org. Chem., 1994, 59, 3590 Search PubMed For a related review, see: S. Kobayashi, Synlett, 1994, 689 CrossRef CAS.
  7. All products have been fully characterized and produced satisfactory 1H and 13C NMR, IR and elemental analysis results. For a Yb(OTf)3 catalyzed allylation of aldehydes with allylsilane to generate homoallyl alcohols, see: Y. Yang, M. Wang and D. Wang, Chem. Commun., 1997, 1651 Search PubMed.
  8. J. Nokami, K. Yoshizane, H. Matsuura and S. Sumida, J. Am. Chem. Soc., 1998, 120, 6609 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.