Synthesis of optically active 9-oxabicyclo[3.3.1]nona-2,6-diene as a cycloocta-1,5-diene equivalent and the corresponding tetrol

Tetrahedron

Volumn 56, Issue 14, 2000, Pages 1999-2006

  Takahashi, Akira ^a   Aso, Mariko ^a   Tanaka, Masakazu ^a   Suemune, Hiroshi ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

5 cyclooctene 1,2 diol; Bidentate olefinic ligand; Chiral ligand

Indexed keywords

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; OPTICAL ROTATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034737568     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00089-2     Document Type: Article

References (13)

1. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932-7934. Hayashi, T.; Katsumura, A.; Konishi, M.; Kumada, M. Tetrahedron Lett. 1979, 20, 425-428. Ojima, I.; Kogure, T.; Kumagai, M. J. Org. Chem. 1977, 42, 1671-1679.
2. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932-7934. Hayashi, T.; Katsumura, A.; Konishi, M.; Kumada, M. Tetrahedron Lett. 1979, 20, 425-428. Ojima, I.; Kogure, T.; Kumagai, M. J. Org. Chem. 1977, 42, 1671-1679.
3. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932-7934. Hayashi, T.; Katsumura, A.; Konishi, M.; Kumada, M. Tetrahedron Lett. 1979, 20, 425-428. Ojima, I.; Kogure, T.; Kumagai, M. J. Org. Chem. 1977, 42, 1671-1679.
4. For the synthesis of (dl)-15; Eaton, P. S.; Millikan, P. Synthesis 1990, 483-484.
5. Horikawa T., Tanaka M., Sakai K., Suemune H. Chem. Pharm. Bull. 46:1998;17-21.
6. Davies S.G., Polywka M.E.C., Thomas S.E. Tetrahedron Lett. 26:1985;1461-1464.
7. Ackermann P., Ganter C. Helv. Chim. Acta. 59:1976;2531-2535.
8. Wright M.E., Cochran B.B. Organometallics. 15:19;317-324. (and references cited therein).
9. The synthetic procedure from 10 to 22 via 27 and 28 was developed by using racemic compounds.
10. Noyori R., Sato T., Hayakawa Y. J. Am. Chem. Soc. 100:1978;2561-2563.
11. Altomare A., Burla M.C., Camalli M., Cascarano M., Giacovazzo C., Guagliardi A., Polidori G. J. Appl. Crystallogr. (SIR92). 27:1994;435.
12. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. The DIRDIF-94 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1994.
13. Molecular Structure Corporation, 3200 Research Forest Drive, The Woodlands, TX 77381, USA: TEXSAN Crystal Structure Analysis Package, 1985 and 1992.