Oxazaborolidine-catalyzed enantioselective reduction of α-methylene ketones to allylic alcohols

Journal of Organic Chemistry

Volumn 73, Issue 17, 2008, Pages 6902-6904

  Matsuo, Jun Ichi ^a   Kozai, Takaaki ^a   Nishikawa, Osamu ^a   Hattori, Yu ^a   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; ESTERS; KETONES; STEREOSELECTIVITY;

ALLYLIC ALCOHOLS; ENANTIOSELECTIVE REDUCTION; OXAZABOROLIDINE;

ORGANIC COMPOUNDS;

24 HYDROXYCHOLESTERYL ACETATE; 24 HYDROXYCHOLESTERYLESTER; 24 OXOCHOLESTERYLESTER; ALCOHOL; ALLYL COMPOUND; ANILINE DERIVATIVE; BORANE DERIVATIVE; CARBON; CHOLESTEROL ESTER; KETONE DERIVATIVE; OXAZABOROLIDINE DERIVATIVE; REDUCING AGENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; HYDROGENATION; REDUCTION; STEREOCHEMISTRY; STOICHIOMETRY;

ANILINE COMPOUNDS; AZA COMPOUNDS; BORANES; BORON COMPOUNDS; CATALYSIS; CHOLESTEROL ESTERS; HYDROGENATION; KETONES; MODELS, CHEMICAL; OXIDATION-REDUCTION; PROPANOLS; STEREOISOMERISM;

EID: 51549096739     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8011013     Document Type: Article

References (36)

1. Review: Nishikawa, O. Medchem News 1994, 4, 85-90.
2. (a) Matsui, T.; Nakao, Y.; Kobayashi, N.; Kishihara, M.; Ishizuka, S.; Watanabe, S.; Fujita, T Int. J. Cancer 1984, 33, 193-202.
3. (b) Matsunaga, T.; Yamamoto, M.; Ohta, T.; Kiyoki, M.; Ohba, T.; Naruchi, T.; Hosoi, J.; Kuroki, T. J. Dermatol. 1990, 17, 135-142.
4. (a) Morisaki, M.; Koizumi, N.; Ikekawa, N.; Takeshita, T.; Ishimoto, S. J. Chem. Soc., Perkin Trans. 1 1975, 1421-1424.
5. (b) Nishikawa, O.; Ishimaru, K.; Takeshita, T.; Tsuruta, H. U.S. Patent 4,298,537, 1981.
6. (c) Nishikawa, O.; Ishimaru, K.; Takeshita, T.; Ysuruta, H. U.S. Patent 4,388,243, 1983.
7. (d) Okamoto, M.; Tabe, M.; Fujii, T.; Tanaka, T. Tetrahedron: Asymmetry 1995, 6, 767-778.
8. Review: (a) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
9. (b) Itsuno, S. Org. React. 1998, 52, 395-576.
10. (c) Itsuno, S. In Comprehensive Asymmetric Catalysts; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. 3, pp 289-315.
11. (d) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504.
12. (e) Cho, B. T. Tetrahedron 2006, 62, 7621-7643.
13. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553.
14. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926.
15. DeNinno, M. P.; Perner, R. J.; Lijewski, L. Tetrahedron Lett. 1990, 31, 7415-7418.
16. (a) Cho, B. T.; Kim, D. J. Tetrahedron 2003, 59, 2457-2462.
17. (b) Cho, B. T.; Choi, O. K.; Kim, D. J. Tetrahedron: Asymmetry 2002, 13, 697-703.
18. Crich, D.; Ranganathan, K.; Rumthao, S.; Shirai, M. J. Org. Chem. 2003, 68, 2034-2037.
19. Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1995, 36, 9153-9156.
20. Corey, E. J.; Guzman-Perez, A.; Lazerwith, S. E. J. Am. Chem. Soc. 1997, 119, 11769-11776.
21. A solution of 3 in toluene was prepared by the reported procedure, see: Xavier, L. C.; Mohan, J. J.; Mathre, D. J.; Thompson, A. S.; Carroll, J. D.; Corley, E. G.; Desmond, R. Org. Synth. 1997, 74, 50.
22. Mincione, E. J. Org. Chem. 1978, 43, 1829-1830.
23. Purchased from Aldrich. For employment of borane-diethylaniline in oxazaborolidine-catalyzed reduction, see: (a) Periasamy, M.; Kanth, J. V. B.; Prasad, A.S. B. Tetrahedron 1994, 50, 6411-6416.
24. (b) Salunkhe, A. M.; Burkhardt, E. R. Tetrahedron Lett. 1997, 38, 1523-1526.
25. 3-THF complex reduces α,β- unsaturated carbonyl compounds with a formation of saturated carbinols. (a) Klein, J.; Dunkelblum, E Tetrahedron Lett. 1966, 604, 7-6049.
26. (b) Klein, J.; Dunkelblum, E. Tetrahedron 1968, 24, 5701-5710.
27. (c) Dunkelblum, E.; Levene, R.; Klein, J. Tetrahedron 1972, 28, 1009-1024.
28. Shibata, T.; Nakatsuki, K.; Soai, K. Inorg. Chim. Acta 1999, 296, 33-36.
29. (a) Cai, D.; Tschaen, D.; Shi, Y.-J.; Verhoeven, T. R.; Reamer, R. A.; Douglas, A. W. Tetrahedron Lett. 1993, 34, 3243-3246.
30. (b) Falorni, M.; Collu, C.; Giacomelli, G. Tetrahedron: Asymmetry 1996, 7, 2739-2742.
31. (c) Yeung, Y.-Y.; Chein, R.-J.; Corey, E. J. J. Am. Chem. Soc. 2007, 129, 10346-10347.
32. Brown, H. C.; Murray, L. T. Inorg. Chem. 1984, 23, 2746-2753.
33. The use of borane-THF complex did not give a satisfactory result.
34. Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071-6072.
35. 4, see: Ishiguro, M.; Koizumi, N.; Yasuda, M.; Ikekawa, N. J. Chem. Soc. Chem. Commun. 1981, 115-117.
36. Bonnert, R. V.; Jenkins, P. R. J. Chem. Soc., Perkin Trans. 1 1989, 413-418.