Inversion of diastereoselectivity depending on substrate concentration in baker's yeast catalyzed reduction of σ-symmetrical 1,3-cyclopentadiones and 1,3-cyclohexadiones

Synlett

Volumn , Issue 14, 2006, Pages 2176-2182

  Katoh, Takahiro ^a   Mizumoto, Shinsuke ^a   Fudesaka, Masato ^a   Nakashima, Yuki ^a   Kajimoto, Tetsuya ^a   Node, Manabu ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

symmetrical cyclopentane 1,3 dione; Baker's yeast catalyzed asymmetric reduction; Substrate concentration

Indexed keywords

1,3 CYCLOHEXADIONE DERIVATIVE; 1,3 CYCLOPENTADIONE DERIVATIVE; ACETYLACETONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY; YEAST;

EID: 33748707989     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949647     Document Type: Article

References (28)

1. See, for example: Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry, In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1994.
2. (a) Sih, C. J. Angew. Chem., Int. Ed. Engl. 1984, 23, 570.
3. (b) Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695.
4. (c) Whitesides, G. M.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1985, 24, 617.
5. (d) Jones, J. B. Tetrahedron 1986, 42, 3351.
6. Prelog, V. Pure Appl. Chem. 1968, 9, 119.
7. (a) Brooks, D. W.; Mazdiyanski, H.; Grothaus, P. G. J. Org. Chem. 1987, 52, 3223.
8. (b) Brooks, D. W.; Grothaus, P. G.; Irwin, W. L. J. Org. Chem. 1982, 47, 2820.
9. (a) Kitahara, T.; Miyake, M.; Kido, M.; Mori, K. Tetrahedron: Asymmetry 1990, 1, 775.
10. (b) Mori, K.; Fujiwhara, M. Tetrahedron 1988, 44, 343.
11. (c) Mori, K.; Mori, H. Org. Synth. 1990, 68, 56.
12. (d) Fuhshuku, K.; Funa, N.; Akeboshi, T.; Ohta, H.; Hosomi, H.; Ohba, S.; Sugai, T. J. Org. Chem. 2000, 65, 129.
13. (a) Iwamoto, M.; Kawada, H.; Tanaka, T.; Nakada, M. Tetrahedron Lett. 2003, 44, 7239.
14. (b) Watanabe, H.; Iwamoto, M.; Nakada, M. J. Org. Chem. 2005, 70, 4652.
15. (c) Wei, Z.-L.; Li, Z. Y.; Lin, G.-Q. Tetrahedron: Asymmetry 2001, 12, 229.
16. (d) Wei, Z.-L.; Li, Z.-Y.; Lin, G.-Q. Synthesis 2000, 1673.
17. (e) Moue, T.; Hosomi, K.; Araki, M.; Nishide, K.; Node, M. Tetrahedron: Asymmetry 1995, 6, 31.
18. Gramatica, P.; Manitto, P.; Monti, D.; Speranta, G. Tetrahedron 1988, 44, 1299.
19. (a) Brooks, D. W.; Grothaus, P. G.; Irwin, W. L. J. Org. Chem. 1982, 47, 2820.
20. (b) Not only baker's yeast but also Saccharomyces cerevisiae (brewing yeast), Bacillus thuringiensis afforded excellent results:
21. (c) Kosmol, H.; Kieslish, K.; Vossing, R.; Koch, H. J.; Petzoldt, K.; Gibian, H. Justus Liebigs Ann. Chem. 1967, 701, 198.
22. (d) Dai, W. M.; Zhou, W. S. Tetrahedron 1985, 41, 4475.
23. 3): δ = 18.7, 18.9, 27.2, 29.2, 33.1, 34.0, 51.9, 53.8, 76.8, 175.1, 221.3.
24. In order to obtain high reproducibility in the reaction with 8 mM substrate, newly opened baker's yeast must be used. If long-term-stored yeast (longer than ca. 6 months at 4 °C) is used in the reaction, a reduced de is observed. The reproduced results were obtained with baker's yeast (Sigma, type II, lot. No. 125K0062).
25. 3): δ = 19.2, 26.7, 28.2, 28.4, 33.9, 51.4, 52.7, 77.3, 121.0, 149.2, 167.1, 220.0.
26. Chiral HPLC analysis of 9b was performed with a Shimadzu LC-10A Liquid Chromatograph series using a SHISEIDO Ceramospher Chiral RU-1 (0.46 φ × 250 mm). Two enantiomers of 9b were detected at the retention time of 10.7 and 11.7 min by eluting with MeOH, flow rate: 0.5 mL/min, at 50 ×C. The enantiomer predominantly obtained in the reaction (entry 1, Table 1) appeared at 11.7 min. Meanwhile, two enantiomers of 9a were detected using Daicel CHIRALCEL OJ-H (0.46 φ × 250 mm) at 43.2 and 47.5 min by eluting with a mixed solvent of n-hexane and 2-PrOH (9:1), flow rate: 0.5 mL/min, at 25 °C. The predominant enantiomer in the reaction (entry 2, Table 1) was detected at 47.5 min.
27. Chiral HPLC analyses of 13b and 14b were performed with Daicel CHIRALCEL OD-H (n-hexane-i-PrOH = 96:4).
28. Katoh, T.; Mizumoto, S.; Fudesaka, M.; Takeo, M.; Kajimoto, T.; Node, M. Tetrahedron: Asymmetry 2006, in press.