Practical and catalytic synthesis of 1,5-anhydrohex-1-en-3-uloses

Tetrahedron

Volumn 55, Issue 28, 1999, Pages 8331-8340

  Hayashi, Masahiko ^a   Yamada, Kanako ^a   Arikita, Osamu ^a  

^a YAMAGUCHI UNIVERSITY   (Japan)

Author keywords

Carbohydrates; Glycals; Oxidation; Palladium catalyst

Indexed keywords

1,5 ANHYDROHEX 1 EN 3 ULOSE DERIVATIVE; ALKENE DERIVATIVE; CARBOHYDRATE DERIVATIVE; ETHYLENE; GLUCONATE CALCIUM; HYDROGEN; PALLADIUM COMPLEX; UNCLASSIFIED DRUG; VINYL ACETATE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033538621     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00426-3     Document Type: Article

References (19)

1. 1. Holder, N. L. Chem. Rev. 1982, 82, 287-332.
2. 2. Tatsuta, K.; Hayakawa, J.; Tatsuzawa, Y. Bull. Chem. Soc. Jpn. 1989, 62, 490-492.
3. 3. Benhaddou, R.; Czernecki, S.; Ville, G. J. Org. Chem. 1992, 57, 4612-4616.
4. 4. Czernecki, S.; Vijayakumaran, K.; Ville, G. J. Org. Chem. 1986, 51, 5472-5475.
5. 5. Bellosta, V.; Benhaddou, R.; Czernecki, S. Synlett 1993, 861-863.
6. 6. Recently reported catalytic oxidation method of alcohols; Sato, K.; Aoki, M.; Takagi, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386-12387.
7. 7. Hudlucky, M. In Oxidations in Organic Chemistry; ACS Monograph; Washington, DC, 1990. Sheldon, R. A.; Kochi, J. K. In Metal-Catalyzed Oxidations of Organic Compounds; Academic Press; New York, 1994.
8. 7. Hudlucky, M. In Oxidations in Organic Chemistry; ACS Monograph; Washington, DC, 1990. Sheldon, R. A.; Kochi, J. K. In Metal-Catalyzed Oxidations of Organic Compounds; Academic Press; New York, 1994.
9. 8. Lloyd, W. G. J. Org. Chem. 1967, 32, 2816-2819.
10. 9. Blackburn, T. F.; Schwartz, J. Chem. Commun. 1977, 157-158.
11. 10. Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011-6014.
12. 11. Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185-3189.
13. 12. Hayashi, M.; Kawabata, H.; Arikita, O. Tetrahedron Lett. 1999, 40, 1729-1730.
14. 13. Hayashi, M.; Amano, K.; Tsukada, K.; Lamberth, C. J. Chem. Soc. Perkin Trans 1 1999, 239-240.
15. 14. Hayashi, M.; Yamada, K.; Arikita, O. Tetrahedron Lett. 1999, 40, 1171-1174.
16. 15. Hydrogen transfer reaction using ruthenium complex; Naota, T.; Takaya, H.; Murahashi, S-I. Chem. Rev. 1998, 98, 2599-2660.
17. 2 in the absence of vinyl acetate afforded the mixture of products (oxidized product/hydrogenated one) in a ratio of 58/42 (85% yield) and 49/51 (65% yield), respectively.
18. 17. Tronchet, J. M. J.; Tronchet, J.; Birkhauser, A. Helv. Chim. Acta 1970, 53, 1489-1490.
19. 18. Paulsen, H.; Bünsch, H. Chem. Ber. 1978, 111, 3484-3496.