Stereoselective synthesis of 5-7 membered cyclic ethers by deiodonative ring-enlargement using hypervalent iodine reagents

Molecules

Volumn 10, Issue 1, 2005, Pages 183-189

  Abo, Tomohito ^a   Sawaguchi, Masanori ^a   Senboku, Hisanori ^a   Hara, Shoji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Cyclic ether; Hypervalent iodine compounds; Ring enlargement

Indexed keywords

ETHER DERIVATIVE; HEXAFLUORO 2 PROPANOL; IODINE DERIVATIVE; SOLVENT;

ARTICLE; STEREOCHEMISTRY; SYNTHESIS;

EID: 15544370001     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/10010183     Document Type: Article

References (17)

1. Inagaki, T.; Nakamura, Y.; Sawaguchi, M.; Yoneda, N.; Ayuba, S.; Hara, S. Tetrahedron Lett. 2003, 44, 4117-4119.
2. Nakata, T.; Nomura, S.; Matsukura, H.; Tetrahedron Lett. 1996, 37, 213-216.
3. Matsukura, H.; Morimoto, M.; Koshino, H.; Nakata, T. Tetrahedron Lett. 1997, 38, 5545-5548.
4. Hori, N.; Nagasawa, K.; Shimizu, T.; Nakata, T. Tetrahedron Lett. 1999, 40, 2145-2148.
5. Takahashi, S.; Fujisawa, K.; Sakairi, N.; Nakata, T. Heterocycles 2000, 53, 1361-1370.
6. Amouroux, R.; Gerin, B.; Chastrette, M. Tetrahedron Lett. 1982, 23, 4341-4344.
7. Evans, R. D.; Magee, J. W.; Schauble, J. H. Synthesis, 1988, 862-868.
8. Brunel, Y.; Rousseau, G. J. Org. Chem. 1996, 61, 5793-5800.
9. Conti, P.; Dallanoce, C.; Amici, M. D.; Micheli, C. D.; Carrea, G.; Zambianchi, F. Tetrahedron: Asymmetry 1998, 9, 657-665.
10. Cossy, J.; Tresnard, L.; Belotti, D.; Pardo, D. G. Tetrahedron Lett. 2001, 42, 251-254.
11. Knight, D. W.; Staples, E. R. Tetrahedron Lett. 2002, 43, 6771-6773.
12. (a) Macdonald, T. L.; Narasimhan, N. J. Org. Chem. 1985, 50, 5000-5001;
13. (b) Sawaguchi, M.; Hara, S.; Nakamuar, Y.; Ayuba, S.; Fukuhara, T.; Yoneda, N. Tetrahedron 2001, 57, 3315-3319.
14. As for the role of HFIP as co-solvent, see: Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
15. Sharefkin, J. G.; Saltzmann, H. Org. Synth., Coll. Vol. 5, 1973, 660-663.
16. Michael, J. P.; Ting, P. C.; Bartlett, P. A. J. Org. Chem. 1985, 50, 2416-2423.
17. Jung, M. E.; Kiankarimi, M. J. Org. Chem. 1998, 63, 8133-8144.