Asymmetric reduction of α,β-unsaturated cyclic ketones by a yeast

Chemistry Letters

Volumn , Issue 4, 1998, Pages 283-284

  Matsumoto, Kazutsugu ^a   Kawabata, Yoichi ^a   Takahashi, Jun ^a   Fujita, Yoshitomo ^a   Hatanaka, Minoru ^a  

^a UNIVERSITY OF FUKUI   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000227779     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.283     Document Type: Article

References (24)

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11. K. Matsumoto and H. Ohta, unpublished data.
12. Reductions of acyclic ketones by Y. farinosa have been reported. See, Y. Ohtsuka, O. Katoh, T. Sugai, and H. Ohta, Bull. Chem. Soc. Jpn., 70, 483 (1997), and references cited therein.
13. E. W. Warnhoff, D. G. Martin, and W. Johnson, "Organic Synthesis," Coll. Vol. IV, 162 (1963).
14. 4 in distilled water.
15. 2; dodecane (6.7 min), 2 (10.1 min), cis-3 (13.5 min), trans-3 (13.9 min), 1 (15.9 min).
16. 20 +42.9°(c1, MeOH). The diastereomers of 3 were easily separated by column chromatography on silica-gel. The ee of cis-3 was determined by the method described in Ref.13. On the other hand, the ee of trans-3 was determined by HPLC analysis of the corresponding MTPA ester. Conditions of HPLC analysis: column, Zorbax-Sil (0.46 mm × 25 cm, DuPont Instruments); eluent, hexane/AcOEt = 200/1; flow rate, 0.5 ml/min.
17. Changes in the pH (5.5 - 8.0) of the reaction media did not affect the reaction.
18. C. Beard, C. Djerassi, J. Sicher, F. Sipos, and M. Tichy, Tetrahedron, 19, 919 (1963).
19. 2.
20. 2 = 7.5 Hz, 1H) due to the placement of this proton in the deshielding region of the neighboring carbonyl group. See, J. K. Crandall, J. P. Arrington, and J. Hen, J. Am. Chem. Soc., 89, 6208 (1967).
21. The microbial reaction for 24 h afforded the mixture of 8 and 9 (cis/trans = 1/2.0). The product ratio of 8/9 was 1/11.
22. A. I. Meyers, D. R. Williams, G. W. Erickson, S. White, and M. Druelinger, J. Am. Chem. Soc., 103, 3081 (1981).
23. 3BH and esterification.
24. R. Bäckström and B. Sjöberg, Ark. Kemi, 26, 549 (1967).