Asymmetric cyclization of meso-diepoxides using chiral (salen)Co(III)OAc catalyst forming optically active 1,4-anhydropentitols and 2,5- anhydrohexitols

Tetrahedron Asymmetry

Volumn 10, Issue 19, 1999, Pages 3667-3669

  Kamada, Masatoshi ^a   Satoh, Toshifumi ^a   Kakuchi, Toyoji ^a   Yokota, Kazuaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2:4,5 DIANHYDRO 3 O METHYLXYLITOL; 1,2:5,6 DIANHYDRO 3,4 DI O METHYLALLITOL; 1,2:5,6 DIANHYDRO 3,4 DI O METHYLGALACTITOL; EPOXIDE; UNCLASSIFIED DRUG; XYLITOL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; OPTICAL ROTATION; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033452450     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00393-6     Document Type: Article

References (9)

1. Kakuchi, T.; Satoh, T.; Umeda, S.; Hashimoto, H.; Yokota, K. Macromolecules 1995, 28, 5643.
2. Kamada, M.; Satoh, T.; Yokota, K.; Kakuchi, T. Macromolecules 1999, 32, 5755.
3. Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420.
4. Schaus, S. E.; Larrow, J. E.; Jacobsen, E. N. J. Org. Chem. 1997, 62, 4197.
5. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
6. Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773.
7. The preparation of diepoxide 2 has been reported: Satoh, T.; Shibata, K.; Yokota, K.; Kakuchi, T. Macromol. Rapid Commun. 1999, 20, 55.
8. The preparations of (R,R)-1 and (S,S)-1 have been reported: Leung, W. H.; Chan, E. Y. Y.; Chow, E. K. F.; Williams, I. D.; Peng, S. M. J. Chem. Soc., Dalton Trans. 1996, 1229.
9. -3 mol) and then the mixture was stirred for 60 h occasionally checking the progress of reaction by TLC chromatogram. After the reaction mixture was diluted with water, the whole was filtered through the membrane (nitrocellulose), and the filtrate was evaporated. Repetition of these procedures a few times gave D-5 (0.42 g, 86%) as a colorless oil.