Preparation of new chiral building blocks: Highly enantioselective reduction of prochiral 1,3-cycloalkanediones possessing a methyl group and a protected hydroxymethyl group at their C2 position with Baker's yeast or CBS catalyst

Journal of Organic Chemistry

Volumn 70, Issue 12, 2005, Pages 4652-4658

  Watanabe, Hideaki ^a   Iwamoto, Mitsuhiro ^a   Nakada, Masahisa ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHARACTERIZATION; DERIVATIVES; REDUCTION; SYNTHESIS (CHEMICAL); YEAST;

CHIRAL BUILDING BLOCKS; CONVERGENT SYNTHESIS; ENANTIOSELECTIVE REDUCTION; KETOLS; OPTICAL PURITY;

STEREOCHEMISTRY;

CYCLOALKANE DERIVATIVE; METHYL GROUP;

ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; REDUCTION; SACCHAROMYCES CEREVISIAE; SYNTHESIS;

CATALYSIS; CHEMISTRY, ORGANIC; CYCLOPARAFFINS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SACCHAROMYCES CEREVISIAE; STEREOISOMERISM; TERPENES;

EID: 20344385760     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050349a     Document Type: Article

References (42)

1. We have also prepared the versatile chiral building blocks via the catalytic asymmetric intramolecular cyclopropanation. See: (a) Honma, M.; Sawada, T.; Fujisawa, Y.; Utsugi, M.; Watanabe, H.; Urnino, A.; Matsumura, T.; Hagihara, T.; Takano, M.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 2860-2861.
2. (b) Honma, M.; Nakada, M. Tetrahedron Lett. 2003, 44, 9007-9011.
3. For reviews of biocatalysis, see: (a) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Msnzocchi, A. Chem. Rev. 1992, 92, 1071-1140.
4. (b) Robert, S. M. J. Chem. Soc., Perkin Trans. 1 1998, 157-169.
5. (c) Robert, S. M. J. Chem. Soc., Perkin Trans. 1 1999, 1-21.
6. (d) Robert, S. M. J. Chem. Soc., Perkin Trans. 1 2000, 611-633.
7. (e) Robert, S. M. J. Chem. Soc., Perkin Trans. 1 2001, 1475-1499.
8. (f) Powell, K. A.; Ramer, S. W.; del Cardayré, S. B.; Stemmer, W. P. C.; Tobin, M. B.; Longchamp, P. F.; Huisman, G. W. Angew. Chem., Int. Ed. 2001, 40, 3949-3959.
9. (g) Nakamura, K.; Yamanaka, R.; Matsuda, T.; Harada, T. Tetrahedron: Asymmetry 2003, 14, 2659-2681.
10. For reviews of baker's yeast, see: (a) Servi, S. Synthesis 1990, 1-25.
11. (b) Cusk, R.; Glänzer, B. I. Chem. Rev. 1991, 91, 49-97.
12. (c) Hoegberg, H.-E.; Berglund, P.; Edlund, H.; Faegerhag, J.; Hedenstroem, E.; Lundh, M.; Nordin, O.; Servi, S.; Voerde, C. Catal. Today 1994, 22 (3), 591-606.
13. (d) Mochizuki, N.; Hiramatsu, S.; Sugai, T.; Ohta, H.; Morita, H.; Itokawa, H. Biosci. Biotechnol. Biochem. 1995, 59 (12), 2282-2291.
14. (e) Bertau, M.; Burli, M. Chimia 2000, 54 (9), 503-507.
15. Recently, Sugai and co-workers reported a new and efficient strategy to prepare new chiral building blocks; see: (f) Fuhshuku, K.; Tomita, M.; Sugai, T. Tetrahedron Lett. 2004, 45, 1763-1767.
16. Iwamoto, M.; Kawada, H.; Tanaka, T.; Nakada, M. Tetrahedron Lett. 2003, 44, 7239-7243. Our recent investigation improved the yield of the product 2 to 90%.
17. (a) Kawada, H.; Iwamoto, M.; Utsugi, M.; Miyano, M.; Nakada, M. Org. Lett. 2004, 6, 4491-4494.
18. (b) Takano, M.; Umino, A.; Nakada, M. Org. Lett. 2004, 6, 4897-4900.
19. (a) Brooks, D. W.; Mazdiyasni, H.; Sally, P. J. Org. Chem. 1985, 50, 3411-3414.
20. (b) Brooks, D. W.; Mazdiyasni, H.; Grothaus, P. G. J. Org. Chem. 1987, 52, 3223-3232.
21. For extensive studies on the prochiral 2,2-disubstituted-1,3- cyclohexanediones, see: (c) Fuhshuku, K.-I.; Funa, N.; Akeboshi, T.; Ohta, H.; Hosomi, H.; Ohba, S.; Sugai, T. J. Org. Chem. 2000, 65, 129-135.
22. (d) Wei, Z.-L.; Li, Z.-Y.; Lin, G.-Q. Synthesis 2000, 1673-1676.
23. Mori, K.; Fujiwara, M, Tetrahedron 1988, 44, 343-354.
24. Tamai, Y.; Mizutani, Y.; Hagiwara, H.; Uda, H.; Harada, N. J. Chem. Res., Synop. 1985, 148-149.
25. Newman, M. S.; Manhart, J. H. J. Org. Chem. 1985, 50, 2113-2114.
26. Hosomi, A.; Sakurai, H. J. Am. Chem. Soc. 1977, 99, 1673-1675.
27. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578.
28. See the Supporting Information.
29. Prelog, V. Pure Appl. Chem. 1964, 9, 119-130.
30. A yeast strain showing an opposite enantiotopic group selectivity toward similar cyclic diketones has been reported. See: Fuhshuku, K.; Tomita, M.; Sugai, T. Adv. Synth. Catal. 2003, 345, 766-774.
31. (a) Dess, D. E.; Martin, J. C. J. Org. Chem. 1991, 56, 7277-7287.
32. (b) Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538.
33. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553.
34. (b) Mathre, D. J.; Jones, T. K.; Xavier, L. C.; BIacklock, T. J.; Reamer, R. A.; Mohan, J. J.; Jones, E. T. T.; Hoogsteen, K.; Baum, M. W.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 751-762.
35. (c) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
36. For enantioselective reduction of 2,2-disubstituted-1,3- cyclopentanediones, see: (d) Shimizu, M.; Yamada, S.; Fujita, Y.; Kobayashi, F. Tetrahedron: Asymmetry 2000, 11, 3883-3886.
37. For solvent effect in CBS catalysis, see: (e) Chan-Mo, Y.; Chunsan, K.; Jae-Hong, K. Chem. Commun. 2004, 21, 2494-2495.
38. (f) Nathan, J. G.; Simon, J. Tetrahedron: Asymmetry 2003, 14 (15), 2115-2118.
39. Lewicka-Piekut, S.; Okamura, W. H. Synth. Commun. 1980, 10, 415-20.
40. Bodor, N.; Solan, K. B.; Kaminiski, J. J.; Shih, C.; Pogany, S. J. J. Og. Chem. 1983, 48, 5280-5284.
41. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
42. Ito, Y.; Fujii, S.; Nakatsuka, M.; Kawamoto, F.; Saegusa, T. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 327-333.