Hypervalent iodine(III) reagent-promoted rearrangement and subsequent oxidative ring cleavage of cyclic 2,3-epoxy-1-alcohol derivatives

Heterocycles

Volumn 66, Issue 1, 2005, Pages 309-317

  Kita, Yasuyuki ^a   Matsuda, Satoshi ^a   Fujii, Eri ^a   Kitagaki, Shinji ^a   Inoguchi, Ryoko ^a   Hata, Kayoko ^a   Fujioka, Hiromichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646881940     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-S(K)23     Document Type: Article

References (27)

1. For reviews on the Lewis acid-mediated rearrangement of epoxides, see. Parker R.E., and Isaacs N.S. Chem. Rev. 59 (1959) 737
2. Rickborn B. In: Pattenden G. (Ed). Comprehensive Organic Synthesis, Carbon-Carbon Bond Formation Vol. 3 (1991), Pergamon Press, Oxford 733
3. For recent examples, see. Kita Y., Kitagaki S., Yoshida Y., Mihara S., Fang D.-F., Kondo M., Okamoto S., Imai R., Akai S., and Fujioka H. J. Org. Chem. 62 (1997) 4991
4. Kita Y., Futamura J., Ohba Y., Sawama Y., Ganesh J.K., and Fujioka H. J. Org. Chem. 68 (2003) 5917
5. Fujioka H., Yoshida Y., and Kita Y. J. Syn. Org. Chem. Jpn. 61 (2003) 133
6. Kita Y., Futamura J., Ohba Y., Sawama Y., Ganesh J.K., and Fujioka H. Tetrahedron Lett. 44 (2003) 411
7. Kita Y., Matsuda S., Inoguchi R., Ganesh J.K., and Fujioka H. Tetrahedron Lett. 46 (2005) 89
8. For our reviews on hypervalent iodine(III)reagent, see. Kita Y., Tohma H., and Yakura T. Trends in Organic Chemistry (1992) 113
9. Kita Y., Takada T., and Tohma H. Pure & Appl. Chem. 68 (1996) 627
10. Tohma H., and Kita Y. J. Syn. Org. Chem. Jpn. 62 (2004) 116
11. Kita Y., Matsuda S., Fujii E., Horai M., Hata K., and Fujioka H. Angew. Chem., Int. Ed. 44 (2005) 5857
12. For the reaction of simple epoxides and PIFA, see. Spyroudis S., and Varvoglis A. J. Org. Chem. 46 (1981) 5231
13. For our reports on the reactions of PIFA using HFIP as a solvent, see. Kita Y., Tohma H., Inagaki M., Hatanaka K., and Yakura T. Tetrahedron Lett. 32 (1991) 4321
14. Kita Y., Tohma H., Hatanaka K., Takada T., Fujita S., Mitoh S., Sakurai H., and Oka S. J. Am. Chem. Soc. 116 (1994) 2684
15. 2, see. Ohno M., Oguri I., and Eguchi S. J. Org. Chem. 64 (1999) 8995
16. 2, see. Criegee R., and Beucker H. Ann. Chem. 541 (1939) 218
17. For the reviews on tandem, domino and cascade reactions, see. Tietze L.F., and Beifuss U. Angew. Chem., Int. Ed. Engl. 32 (1993) 131
18. Bunce R.A. Tetrahedron 51 (1995) 13103
19. Tietze L.F. Chem. Rev. 96 (1996) 115
20. Parsons P.J., Penkett C.S., and Shell A.J. Chem. Rev. 96 (1996) 195
21. For examples, see. Matsubara S., Yamamoto H., and Oshima K. Angew., Chem., Int. Ed. 41 (2002) 2837
22. Fan C.-A., Hu X.-D., Tu Y.-Q., Wang B.-M., and Song Z.-L. Chem. Eur. J. 9 (2003) 4301
23. Li X., Wu B., Zhao X.Z., Jia Y.X., Tu Y.Q., and Li D.R. Synlett 623 (2003)
24. Li D.R., Xia W.J., Tu Y.Q., Zhang F.M., and Shi L. Chem. Commun. (2003) 798
25. Hu X.-D., Fan C.-A., Zhang F.-M., and Tu Y.-Q. Angew. Chem., Int. Ed. 43 (2004) 1702
26. Danishefsky S., and Zimmer A. J. Org. Chem. 41 (1976) 4059
27. Sharpless K.B., and Michaelson R.C. J. Am. Chem. Soc. 95 (1973) 6136