Non-Carbohydrate Route to Levoglucosenone and Its Enantiomer Employing Asymmetric Dihydroxylation

Synlett

Volumn 1996, Issue 10, 1996, Pages 971-972

  Taniguchi, Takahiko ^a   Nakamura, Keiichi ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842427481     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5652     Document Type: Article

References (18)

1. Pertinent review, see: 'Levoglucosenone and Levoglucosans, Chemistry and Applications,' Witczak, Z. J., Ed.; ATL Press Inc. Science Publishers, Mount Prospect, Illinois, 1994; Ebata, T.; Matsushita, H. J. Syn. Org. Chem. Jpn. 1994, 52, 1074.
2. Pertinent review, see: 'Levoglucosenone and Levoglucosans, Chemistry and Applications,' Witczak, Z. J., Ed.; ATL Press Inc. Science Publishers, Mount Prospect, Illinois, 1994; Ebata, T.; Matsushita, H. J. Syn. Org. Chem. Jpn. 1994, 52, 1074.
3. Shibagaki, M.; Takahashi, K.; Kuno, H.; Honda, I.; Matsushita, H. Chem. Lett. 1990, 307.
4. Witczak, Z. J.; Mielguj, R. Synlett 1996, 108.
5. Schmidt, U.; Werner, J. Synthesis 1986, 986.
6. a) Köll, P.; Schultek, T.; Rennecke, R. -W. Chem. Ber. 1976, 337.
7. b) Horton, D., Roski, J. P.; Norris, P. J. Org. Chem. 1996, 61, 3783.
8. A pertinent review, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
9. Lefebvre, Y. Tetrahedron Lett. 1972, 133; Martin, S. F.; Gluchowski, C.; Campbell, C. L.; Chapman, R. C. J. Org. Chem. 1984, 49, 2512; Martin, S. F.; Zinke, P. W. J. Org. Chem. 1991, 56, 6600 and references therein.
10. Lefebvre, Y. Tetrahedron Lett. 1972, 133; Martin, S. F.; Gluchowski, C.; Campbell, C. L.; Chapman, R. C. J. Org. Chem. 1984, 49, 2512; Martin, S. F.; Zinke, P. W. J. Org. Chem. 1991, 56, 6600 and references therein.
11. Lefebvre, Y. Tetrahedron Lett. 1972, 133; Martin, S. F.; Gluchowski, C.; Campbell, C. L.; Chapman, R. C. J. Org. Chem. 1984, 49, 2512; Martin, S. F.; Zinke, P. W. J. Org. Chem. 1991, 56, 6600 and references therein.
12. AD-mix-α and AD-mix-β used were purchased from Aldrich.
13. CHIRALCEL OD (Daicel), elution with i-PrOH/hexane, 1:99.
14. Rolf, K. H.; Rennecke, W.; Köll, P. Chem. Ber. 1975, 108, 3645.
15. Ohloff, G.; Uhde, G. Helv. Chim. Acta 1970, 53, 531; Kawamura, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1995, 2403.
16. Ohloff, G.; Uhde, G. Helv. Chim. Acta 1970, 53, 531; Kawamura, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1995, 2403.
17. Taniguchi, T.; Ohnishi, H.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1996, 1477.
18. 2 (2 ml) was stirred at room temperature for 3 h. After filtration, the mixture was evaporated under atmospheric pressure and chromatographed on silica gel