A lipase-mediated synthesis of single enantiomeric trans-epoxides via convergence of racemic mixtures

Tetrahedron Letters

Volumn 40, Issue 23, 1999, Pages 4383-4386

  Taniguchi, Takahiko ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Asymmetric induction; Enzyme and enzyme reactions; Epoxides; Resolution

Indexed keywords

ALKENE; EPOXIDE; GLYCOL; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHIRALITY; ENANTIOMER; ENZYME MECHANISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RACEMIC MIXTURE; SYNTHESIS;

EID: 0033523060     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00754-6     Document Type: Article

References (12)

1. Takano, S.; Tanigawa, K.; Ogasawara, K. J. Chem. Soc. Chem. Commun. 1976, 189.
2. Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769.
3. Harada, T.; Nakamura, T.; Kinugasa M.; Oku, A. Tetrahedron Lett. 1999, 40, 503.
4. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 25, 1973.
5. Nicolaou, K. C.; Papahatjis, D. P.; Claremon, D. A.; Magolda, R. L.; Doll, R. E. J. Org. Chem. 1985, 50, 1440: Wenger, R. M. Helv. Chim. Acta 1985, 24, 77.
6. Nicolaou, K. C.; Papahatjis, D. P.; Claremon, D. A.; Magolda, R. L.; Doll, R. E. J. Org. Chem. 1985, 50, 1440: Wenger, R. M. Helv. Chim. Acta 1985, 24, 77.
7. Katsuki, T.; Lee, A. W.; Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Tuddenham, D.; Walker, F. J. J. Org. Chem. 1982, 47, 1387: Takano, S.; Kasahara, C.; Ogasawara, K. Chem. Lett. 1983, 175: Ko, S. Y.; Lee, A. W.; Masamune, S.; Reed, III, L. A.; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245.
8. Katsuki, T.; Lee, A. W.; Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Tuddenham, D.; Walker, F. J. J. Org. Chem. 1982, 47, 1387: Takano, S.; Kasahara, C.; Ogasawara, K. Chem. Lett. 1983, 175: Ko, S. Y.; Lee, A. W.; Masamune, S.; Reed, III, L. A.; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245.
9. Katsuki, T.; Lee, A. W.; Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Tuddenham, D.; Walker, F. J. J. Org. Chem. 1982, 47, 1387: Takano, S.; Kasahara, C.; Ogasawara, K. Chem. Lett. 1983, 175: Ko, S. Y.; Lee, A. W.; Masamune, S.; Reed, III, L. A.; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245.
10. Fukuyama, T.; Laird, M.; Hotchkiss, L. M. Tetrahedron Lett. 1984, 25, 2295.
11. Hoyer, S.; Laszlo, P. Synthesis 1986, 655.
12. Montmorillonite K10 in methanol was found to be the most suitable for the removal of tetrahydropyranyl (THP) protecting group without touching epoxy functionality in the molecule.