Diastereoselective synthesis of cyclic 1,3-aminoalcohols bearing CF3(CCl3)-groups

Journal of Fluorine Chemistry

Volumn 129, Issue 7, 2008, Pages 637-644

  Shevchenko, Nikolay E ^a   Röschenthaler, Gerd Volker ^b   Mitiaev, Alexander S ^a   Lork, Enno ^b   Nenajdenko, Valentine G ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b UNIVERSITY OF BREMEN   (Germany)

Author keywords

Aldol reaction; Azaheterocycles; Cyclic imines; Diastereoselectivity; Methyl trifluoropyruvate; Reduction; Trihalomethylcarbinols

Indexed keywords

EID: 46749140823     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.05.005     Document Type: Article

References (42)

1. See, for example: P. Kirsch, Modern Fluoroorganic Chemistry, Wiley VCH, Weinheim, 2004, 308 pp. special edition on organofluorine chemistry in Chem. Rev. 96 (1996) 1557-1824.
2. In: Banks R.E., Smart B.E., and Tatlow J.C. (Eds). Organofluorine Chemistry: Principles and Commercial Applications (1994), Plenum Press, New York 670
3. For some synthetic aspects of organofluorine compounds see: V. A. Soloshonok (Ed.), Fluorine-Containing Synthons, ACS Symposium Series 911, American Chemical Society, Washington, DC, 2005, 666 pp.
4. Hiyama T. Organofluorine Compounds: Chemistry and Applications (2000), Springer, Berlin 272 pp.
5. Soloshonok V.A. In: Soloshonok V.A. (Ed). Enantiocontrolled Synthesis of Fluoro-Organic Compounds (1999), John Wiley & Sons, Chichester 229-263 and references herein
6. Nenajdenko V.G., Gulevich A.V., and Balenkova E.S. Tetrahedron 62 (2006) 5922
7. Nenajdenko V.G., Zakurdaev E.P., Gololobov A.M., and Balenkova E.S. Russ. Chem. Bull. 54 (2005) 220
8. Zakurdaev E.P., Nenajdenko V.G., and Balenkova E.S. Russ. Chem. Bull. 54 (2005) 1219
9. Nenajdenko V.G., Zakurdaev E.P., Prusov E.V., and Balenkova E.S. Russ. Chem. Bull. 53 (2004) 2866
10. Shvekhgeimer M.-G.A. Chem. Heterocycl. Compd. 39 (2003) 405
11. Nenajdenko V.G., Gololobov A.M., Balenkova E.S., and Zakurdaev E.P. Izv. Acad. Nauk Ser. Khim. 52 (2003) 2473
12. Maryanoff B.E., McComsey D.F., Gardocki J.F., Shank R.P., Costanzo M.J., Nortey S.O., Schneider C.R., and Setler P.E. J. Med. Chem. 30 (1987) 1433 for earlier references see review
13. Ikeda M., Sato T., and Ishibashi H. Heterocycles 27 (1988) 1465
14. Barten J.A., Lork E., and Röschenthaler G.-V. J. Fluorine Chem. 125 (2004) 1039
15. Barten J.A., Funabiki K., and Röschenthaler G.-V. J. Fluorine Chem. 113 (2002) 105
16. Feringa B.L., and Jansen F.G.A. Tetrahedron Lett. 27 (1986) 507
17. Koldobskij A.B., Vakhmistrov V.E., Solodova E.V., Sholova O.S., and Kalinin V.N. Dokl. Acad. Nauk 387 (2002) 61
18. Nenajdenko V.G., Zakurdaev E.P., Prusov E.V., and Balenkova E.S. Tetrahedron 60 (2004) 11719
19. Sorgi K.L., Maryanoff C.A., McComsey D.F., and Maryanoff B.E. Org. Synth. 75 (1998) 215
20. Nelson S.G., and Wang K. J. Am. Chem. Soc. 128 (2006) 4232
21. Meyers A.I., Lawson J.P., Walker D.G., and Linderman R.J. J. Org. Chem. 51 (1986) 5111
22. Wittig G., and Frommeld H.-D. Chem. Ber. 97 (1964) 3548
23. Brandange S., and Rodriguez B. Act. Chem. Scan. 37(B) (1983) 643
24. Glasoe P.K., and Long F.A. J. Phys. Chem. 64 (1960) 188
25. House H.O., Crumrine D.S., Teranishi A.Y., and Olmstead H.D. J. Am. Chem. Soc. 95 (1973) 3310
26. CCDC 680285 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html. (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk).
27. Wilson A.J.C. International Tables for Crystallographie, vol. C (1995), Kluwer Academic Publishers, Dordrecht 685 pp.
28. Falck J.R., He A., Reddy M., Kundu A., Barma D.K., Bandyopadhyay A., Kamila S., Akella R., Bejot R., and Mioskowski C. Org. Lett. 8 (2006) 4645 See, for example
29. Bejot R., Tisserand S., Reddy L.M., Barma D.K., Baati R., Falck J.R., and Mioskowski C. Angew. Chem. Int. Ed. 44 (2005) 2008
30. Blanchet J., and Zhu J. Tetrahedron Lett. 45 (2004) 4449
31. CCDC 671216 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html. (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk).
32. Heathcock C.H., Buse C.T., Kleschick W.A., Pirrung M.C., Sohn J.E., and Lampe J. J. Org. Chem. 45 (1980) 1066 This stereostructural nomenclature usually used for classical aldol, see
33. Masamune S., Kaiho T., and Garvey D.S. J. Am. Chem. Soc. 104 (1982) 5521
34. In: Rainer M. (Ed). Modern Aldol Reactions (2004), Wiley-VCH Verlag, Weinheim 699
35. Jaen J.C., Gregor V.E., Lee C., Davis R., and Emmerling M. Bioorg. Med. Chem. Lett. 6 (1996) 737 See, for example
36. The Alkaloids, Special Periodik Report, The Chemistry Society of London, London, V. 1-14.
37. Shishkin V.E., Mednikov E.V., and Anishchenko O.V. Dokl. Chem. (Engl. Transl.) 380 (2001) 290
38. Nesterov L.V., and Sabirova R.A. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 24 (1975) 898
39. Sheldrick G.M. SHELX-97 (1997), University of Goettingen
40. Haslego M.L., Maryanoff C.A., Scott L., and Sorgi K.L. Heterocycles 35 (1993) 643
41. Benson C. Org. Synth. Coll. IV (1963) 588
42. Etienne A., and Correia Y. Bull. Soc. Chim. Fr. (1969) 3704