Asymmetric synthesis of β-dialkylamino alcohols by transfer hydrogenation of α-dialkylamino ketones

Tetrahedron Asymmetry

Volumn 20, Issue 10, 2009, Pages 1138-1143

  Kosmalski, Tomasz ^a   Wojtczak, Andrzej ^a   Zaidlewicz, Marek ^a  

^a NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 BENZOFURYL) 2 (MORPHOLIN 4 YL)ETHANOL; 1 (2 FURYL) 2 (DIMETHYLAMINO)ETHANOL; 1 (3,4 DIMETHYOXYPHENYL)2 (DIMETHYLAMINO)ETHANOL; 1 (BENZOFURYL) 2 (DIMETHYLAMINO)ETHANOL; 1 N,N DIETHYLAMINOPROPAN 2 OL; 1 PHENYL 2 (PIPERIDIN 1 YL)ETHANOL; 1 PHENYL 2 (PYRROLIDIN 1 YL)ETHANOL; 2 (DIETHYLAMINO) 1 (PHENYL)ETHANOL; 2 (DIMETHYLAMINO) 1 (2 NAPHTHYL)ETHANOL; ALCOHOL DERIVATIVE; ALIPHATIC AMINE; KETONE DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL;

EID: 66149165732     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.03.014     Document Type: Article

References (45)

1. Morris D.J., Hayes A.M., and Wills M. J. Org. Chem. 71 (2006) 7035-7044 and references cited therein
2. Everaere K., Mortreux A., Bulliard M., Brussee J., van der Gen A., Nowogrocki G., and Carpentier J.-F. Eur. J. Org. Chem. (2001) 275-291 and references cited therein
3. Ager D.J., Prakash I., and Schaad D.R. Chem. Rev. 96 (1996) 835-875
4. Cardillo G., and Tomasini C. Chem. Soc. Rev. 25 (1996) 117-128
5. Corey E.J., and Helal C.J. Angew. Chem., Int. Ed. 37 (1988) 1986-2012
6. Zaidlewicz, M.; Krzemiński, M.; Ła{ogonek}czkowski, K. in Encyclopedia of Reagents for Organic Synthesis [online]. First update, J. Wiley, 2007, doi: 10.1002/047084289X.rn 00701.
7. Johnson R.L. In: Block J.H., and Beale Jr. J.M. (Eds). Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry. 11th ed. (2004), Lippincott Williams & Wilkins, Philadelphia 524-547
8. Bergmeier S.C. Tetrahedron 56 (2000) 2561-2576
9. Bayer A. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis (2004), Springer, Berlin-Heidelberg 44-71
10. Ohkuma T., and Noyori R. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 1 (1999), Springer, Berlin-Heidelberg 199-246 2004, pp 1-33
11. Brown H.C., and Pai G.G. J. Org. Chem. 50 (1985) 1394-1399
12. Cho B.T., and Chun Y.S. Tetrahedron: Asymmetry 3 (1992) 341-342
13. Beardsley D.A., Fisher G.B., Goralski Ch.T., Nicholson L.W., and Singaram B. Tetrahedron Lett. 35 (1994) 1511-1514
14. Miyano S., Lu L.D.-L., Viti S.M., and Sharpless K.B. J. Org. Chem. 50 (1985) 4350-4360
15. Baeza A., Najera C., Sansano J.M., and Saá J.M. Chem. Eur. J. 11 (2005) 3849-3862
16. Xiong Y., Wang F., Huang X., Wen Y., and Feng X. Chem. Eur. J. 13 (2007) 829-833
17. Metro T.X., Pardo D.G., and Cossy J. J. Org. Chem. 72 (2007) 6556-6561
18. Yadav A.K., and Manju M. Indian J. Chem. 45B (2006) 2770-2772
19. Klingler F.D. Acc. Chem. Res. 40 (2007) 1367-1376
20. Tanis S.R., Evans B.R., Nieman J.A., Parker T.T., Taylor W.D., Heasley S.E., Herrington P.M., Perrault W.R., Hohler R.A., Dolak L.A., Hester M.R., and Seest E.P. Tetrahedron: Asymmetry 17 (2006) 2154-2182
21. Kenny J.A., Palmer M.J., Smith A.R.C., Walsgrove T., and Wills M. Synlett (1999) 1615-1617
22. Kawamoto A.M., and Wills M. Tetrahedron: Asymmetry 11 (2000) 3257-3261
23. Kawamoto A.M., and Wills M. J. Chem. Soc., Perkin Trans. 1 (2000) 1916-1928
24. Zaidlewicz M., Tafelska-Kaczmarek A., Prewysz-Kwinto A., and Chechłowska A. Tetrahedron: Asymmetry 14 (2003) 1659-1664
25. Zaidlewicz M., Tafelska-Kaczmarek A., and Prewysz-Kwinto A. Tetrahedron: Asymmetry 16 (2005) 3205-3210
26. O'Brien P., and Poumellec P. Tetrahedron Lett. 37 (1996) 5619-5622
27. de Sousa S.E., O'Brien P., and Pilgram Ch.D. Tetrahedron 58 (2002) 4643-4654
28. Lennon I.C., and Ramsden J.A. Org. Process Res. Dev. 9 (2005) 110-112
29. Manna L., and Campiglio A. Farmaco (Pavia) Ed. Sci. 14 (1959) 317-322
30. Himmel H.M. Cardiovasc. Drug Res. 12 (1994) 32-47
31. Stokbroex, R. A.; Luyckx, M.; Gerebarnus, M.; Janssens, F. E. Eur. Pat. Appl. EP 184,257, 1986, Chem. Abstr. 1987, 106, 50191.
32. Kaufman T.S., and Rúveda E.A. Angew. Chem., Int. Ed. 44 (2005) 854-885
33. Brown S.D., Hodgkins J.E., and Reinecke M.G. J. Org. Chem. 37 (1972) 773-775
34. Hashiguchi S., Fujii A., Takehara J., Ikariya T., and Noyori R. J. Am. Chem. Soc. 117 (1995) 7562-7563
35. Chapman N.B., and Triggle D.J. J. Chem. Soc. (1963) 1385-1400
36. Bordwell F.G., and Lynch T.-Y. J. Am. Chem. Soc. 111 (1989) 7558-7562
37. Immediata T., and Day A.R. J. Org. Chem. 5 (1940) 512-527
38. Shriner R.L., and Anderson J. J. Am. Chem. Soc. 61 (1939) 2705-2708
39. Ogloblin K.A., and Potekhin A.A. Zh. Org. Khim. 1 (1965) 408-415
40. Padwa A., Eisenhardt W., Gruber R., and Pashayan D. J. Am. Chem. Soc. 93 (1971) 6998-7005
41. Noyori R., Suga S., Kawai K., Okada S., Kitamura M., Oguni N., Hayashi M., Kaneko T., and Matsuda Y. J. Organomet. Chem. 382 (1990) 19-37
42. Saravanan P., Bisai A., Baktharaman S., Chandrasakhar M., and Singh V.K. Tetrahedron 58 (2002) 4693-4706
43. crysalis ccd171 and red171 package of programs, Oxford Diffraction, 2000.
44. Sheldrick, G. M. shelx97 and shelxl97, University of Göttingen, Germany, Göttingen, 1997.
45. Flack H.D. Acta Crystallogr., Sect. A 39 (1983) 876-881