Lipase-mediated kinetic resolution of tricyclic acyloins, endo-3-hydroxytricyclo[4.2.1.02,5]non-7-en-4-one and enod-3-hydroxytricyclo[4.2.2.02,5]dec-7-en-4-one

Tetrahedron Asymmetry

Volumn 8, Issue 16, 1997, Pages 2773-2780

  Taniguchi, Takahiko ^a   Kanada, Regina Mikie ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYTRICYCLO[4.2.1.0]NON 7 EN 4 ONE; 3 HYDROXYTRICYCLO[4.2.2.0]DEC 7 EN 4 ONE; ORGANIC SOLVENT; TRIACYLGLYCEROL LIPASE; TRICYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; ENANTIOMER; ESTERIFICATION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030886939     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00336-4     Document Type: Article

References (14)

1. Taniguchi, T.; Ogasawara, K. Chem. Commun. 1997, 1399.
2. For reviews on dynamic kinetic resolution: Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. Stecher, H.; Faber, K. Synthesis 1997, 1.
3. For reviews on dynamic kinetic resolution: Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. Stecher, H.; Faber, K. Synthesis 1997, 1.
4. For a review on synthetic utility: Ogasawara, K. J. Syn. Org. Chem. Jpn. 1996, 54, 15.
5. Recent syntheses: Sugahara, T.; Kuroyanagi, Y.; Ogasawara, K. Synthesis 1996, 1101 . Knol, J.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 2527 and references cited therein.
6. Recent syntheses: Sugahara, T.; Kuroyanagi, Y.; Ogasawara, K. Synthesis 1996, 1101 . Knol, J.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 2527 and references cited therein.
7. Precedents for kinetic resolution of acyloins: Gala, D.; DiBenedetto, D. J.; Clark, J. E.; Murphy, B. L.; Schumacher, D. P.; Steinman, M. Tetrahedron Lett. 1996, 37, 611 ; Adam, W.; Diaz, M. T.; Fell, R. T.; Saha-Möller, C. R. Tetrahedron: Asymmetry 1996, 7, 2207.
8. Precedents for kinetic resolution of acyloins: Gala, D.; DiBenedetto, D. J.; Clark, J. E.; Murphy, B. L.; Schumacher, D. P.; Steinman, M. Tetrahedron Lett. 1996, 37, 611 ; Adam, W.; Diaz, M. T.; Fell, R. T.; Saha-Möller, C. R. Tetrahedron: Asymmetry 1996, 7, 2207.
9. A pertinent monograph: Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford, 1994.
10. Miller, R. D.; Dolce, D. L.; Merritt, V. Y. J. Org. Chem. 1976, 41, 1221.
11. Yamane, T.; Takahashi, M.; Ogasawara, K. Synthesis 1995, 444.
12. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271 . Takano, S.; Inomta, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636.
13. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271 . Takano, S.; Inomta, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636.
14. Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.