The baker's yeast reduction of 1-acetoxy-2-alkanones in the presence of a sulfur compound

Tetrahedron Asymmetry

Volumn 8, Issue 19, 1997, Pages 3201-3204

  Hayakawa, Ryuuichirou ^a   Shimizu, Makoto ^a   Fujisawa, Tamotsu ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKANEDIOL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENZYME ACTIVITY; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; YEAST;

EID: 0030876207     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00434-5     Document Type: Article

References (33)

1. (a) Servi, S. Synthesis 1990, 1-25.
2. (b) Csuk, R.; Glänzer, B. I. Chem. Rev. 1991, 91, 49-97.
3. (c) Jones, J. B. In Comprehensive Organic Synthesis Trost, B. M., Ed., Pergamon Press, New York, 1991, Vol. 8, 183-209.
4. (d) Santaniello, E.; Ferraboschi, P. Encyclopedia of Reagents for Organic Synthesis Paquett, L. A., Ed., John Wiley and Sons, Chichester, 1995, Vol. 1, 233-236.
5. (a) Levene, P. A.; Walti, A. Org. Synth. Coll. Vol. II 1943, 545-547.
6. (b) Manzocchi, A.; Fiecchi, A.; Santaniello, E. J. Org. Chem. 1988, 53, 4405-4407.
7. (c) Ishihara, K.; Sakai, T.; Tsuboi, S.; Utaka, M. Tetrahedron Lett. 1994, 35, 4569-4570.
8. (d) Ishihara, K.; Higashi, Y.; Tsuboi, S.; Utaka, M. Chem. Lett. 1995, 253-254.
9. (a) Zhou, B.; Gopalan, A. S.; Middlesworth, F. V.; Shieh, W.-R.; Sih, C. J. J. Am. Chem. Soc. 1983, 105, 5925-5926.
10. (b) Fuganti, C.; Grasselli, P.; Casati, P.; Carmeno, M. Tetrahedron Lett. 1985, 26, 101-104.
11. (a) Nakamura, K.; Inoue, K.; Ushio, K.; Oka, S.; Ohno, A. Chem. Lett. 1987, 679-682.
12. (b) Nakamura, K.; Kawai, Y.; Oka, S.; Ohno, A. Bull. Chem. Soc. Jpn 1989, 62, 875-879.
13. (c) Nakamura, K.; Kawai, Y.; Ohno, A. Tetrahedron Lett. 1990, 31, 267-270.
14. Nakamura, K.; Kawai, Y.; Oka, S.; Ohno, A. Tetrahedron Lett. 1989, 30, 2245-2246.
15. (a) Nakamura, K.; Kawai, Y.; Nakajima, N.; Ohno, A. J. Org. Chem. 1991, 56, 4778-4783.
16. (b) Nakamura, K.; Kawai, Y.; Ohno, A. Tetrahedron Lett. 1991, 32, 2927-2928.
17. (c) Kawai, Y.; Kondo, S.; Tsujimoto, M.; Nakamura, K.; Ohno, A. Bull. Chem. Soc. Jpn 1994, 62, 2244-2247.
18. (a) Jayasinghe, L. Y.; Smallridge, A. J.; Trewhella, M. A. Tetrahedron Lett. 1993, 34, 3949-3950.
19. (b) North, M. Tetrahedron Lett. 1996, 37, 1699-1702.
20. (c) Rotthaus, O.; Krüger, D.; Demuth, M.; Schaffner, K. Tetrahedron 1997, 53, 935-938.
21. (d) Medson, C.; Smallridge, A. J.; Trewhella, M. A. Tetrahedron: Asymmetry 1997, 8, 1049-1054.
22. (a) Sato, T.; Fujisawa, T. Biocatalysis 1990, 3, 1-15.
23. (b) Hayakawa, R.; Shimizu, M.; Fujisawa, T. Tetrahedron Lett. 1996, 37, 7533-7536, and the references cited therein.
24. Moon, S.; Bohm, H. J. Org. Chem. 1972, 37, 4338-4340.
25. 2c
26. It has been reported that an accelerated reaction rate was observed using glucose, the energy-gaining and NAD(P)H-producing glycolysis system of yeast, in the baker's yeast reduction of β-keto ester derivatives. Nakamura, K.; Kawai, Y.; Oka, S.; Ohno, A. Bull. Chem. Soc. Jpn 1989, 62, 875-879.
27. 2b
28. (a) Fournier, L.; Natat, A.; Lamaty, G.; Roque, J. P. Recl. Trav. Chim. Pays-Bas 1972, 91, 1015-1025.
29. (b) Liehard, G. E.; Jencks, W. P. J. Am. Chem. Soc. 1966, 88, 3982-3995.
30. (c) Barnett, R. E.; Jencks, W. P. J. Am. Chem. Soc. 1969, 91, 6758-6765.
31. (d) Rails, J. W.; Dodson, R. M.; Riegel, B. J. Am. Chem. Soc. 1949, 71, 3320-3325.
32. (e) Djerassi, C.; Gorman, M. J. Am. Chem. Soc. 1953, 75, 3704-3708.
33. (f) Chan, T. H.; Ong, B. S. Tetrahedron Lett. 1976, 17, 319-322.