Wittig rearrangement of allyl and propargyl furfuryl ethers leading to 2-furylmethanol derivatives

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

Masayoshi Tsubuki, Teruyoshi Kamata, Hiroyuki Okita, Mayumi Arai, Atsushi Shigihara and Toshio Honda


Abstract

The first example of the Wittig rearrangement of furfuryl ethers is presented and its application to the preparation of 3-(2-furyl)-3-hydroxy-2-methylpropionates is described.


References

  1. M. Tsubuki, H. Okita and T. Honda, J. Chem. Soc., Chem. Commun., 1995, 2135 RSC.
  2. J. A. Marshall, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, New York, 1991, vol. 3, p. 975 Search PubMed; R. Brückner, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, New York, 1991, vol. 6, p. 873 Search PubMed; T. Nakai and K. Mikami, Org. React., 1994, 46, 105 Search PubMed.
  3. Marshall et al. have reported a [2,3] Wittig rearrangement of a macrocycilc furan diether, in which the allyl furfuryl ether moiety did not react via[2,3] Withig rearrangement: J. A. Marshall and D. J. Nelson, Tetrahedron Lett., 1988, 29, 741 Search PubMed.
  4. pKa values for 2-methylfuran and MeCH–CH2 are 43 and 44, respectively. See F. G. Bordwell, Acc. Chem. Res., 1988, 21, 456 Search PubMed.
  5. P. G. M. Wuts and G. R. Callen, Synth. Commun., 1986, 16, 1833 CAS; G. Cahiez and P.-Y. Chavant, Tetrahedron Lett., 1989, 30, 7373 CrossRef CAS.
  6. H. Akita, H. Koshiji, A. Furuichi, K. Horikoshi and T. Oishi, Chem. Pharm. Bull., 1984, 32, 1242 CAS; S. F. Martin and D. E. Guinn, J. Org. Chem., 1987, 52, 5588 CrossRef CAS.
  7. J. E. Zanetti, J. Am. Chem. Soc., 1927, 49, 1061 CrossRef CAS; W. R. Kirner, J. Am. Chem. Soc., 1928, 50, 1955 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.