Stereoselective synthesis of syn-β-amino esters using the TiCl 4/R3N reagent system

Tetrahedron Letters

Volumn 46, Issue 33, 2005, Pages 5521-5524

  Periasamy, Mariappan ^a   Suresh, Surisetti ^a   Subramaniapillai, Selva Ganesan ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Amino esters; Imines and Mannich reaction; Titanium ester enolates

Indexed keywords

AMINO ACID DERIVATIVE; BENZALDEHYDE; BETA AMINO ACID; ESTER DERIVATIVE; IMINE; TITANIUM TETRACHLORIDE;

ARTICLE; DRUG SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 22144444568     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.048     Document Type: Article

References (41)

1. G. Cardillo, and C. Tomasini Chem. Soc. Rev. 1996 117 128
2. F.H. van der Steen, and G. van Koten Tetrahedron 47 1991 7503 7524
3. D.J. Hart, and D.-C. Ha Chem. Rev. 89 1989 1447 1465
4. S. Krauthäuser, L.A. Christianson, D.R. Powell, and S.H. Gellman J. Am. Chem. Soc. 119 1997 11719 11720
5. S.B. Rosenblum, T. Huynh, A. Afonso, H.R. Davis Jr., N. Yumibe, J.W. Clader, and D.A. Burnett J. Med. Chem. 41 1998 973 980
6. M. Arend, W. Bernhard, and N. Risch Angew. Chem., Int. Ed. 37 1998 1044 1070
7. M. Tramontini, and L. Angiolini Mannich Bases Chemistry and Uses 1994 CRC Boca Raton, FL and references cited therein
8. R.A. Volkmann B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 1 1991 Pergamon Oxford, UK 355 and references cited therein
9. S. Kobayashi, R. Matsubara, and H. Kitagawa Org. Lett. 4 2002 143 145
10. F.A. Davis, Y. Zhang, and G. Anilkumar J. Org. Chem. 68 2003 8061 8064
11. G.B. Evans, R.H. Furneaux, P.C. Tyler, and V.L. Schramm Org. Lett. 5 2003 3639 3640
12. S.F. Martin Acc. Chem. Res. 35 2002 895 904
13. T. Fujita, H. Nagasawa, Y. Uto, T. Hashimoto, Y. Asakawa, and H. Hori Org. Lett. 6 2004 827 830
14. N.S. Joshi, L.R. Whitaker, and M.B. Francis J. Am. Chem. Soc. 126 2004 15942 15943
15. A.G. Wenzel, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 12964 12965
16. H. Ishitani, M. Ueno, and S. Kobayashi J. Am. Chem. Soc. 122 2000 8180 8186
17. S. Kobayashi, and H. Ishitani Chem. Rev. 99 1999 1069 1094 and references cited therein
18. S. Hata, M. Iguchi, T. Iwasawa, K.-i. Yamada, and K. Tomioka Org. Lett. 6 2004 1721 1723
19. S. Saito, K. Hatanaka, and Y. Yamamoto Org. Lett. 2 2000 1891 1894
20. S. Hata, T. Iwasawa, M. Iguchi, K.-i. Yamada, and K. Tomioka Synthesis 2004 1471 1475
21. I. Ojima, S.-i. Inaba, and K. Yoshida Tetrahedron Lett. 18 1977 3643 3646
22. I. Ojima, and S.-i. Inaba Tetrahedron Lett. 21 1980 2077 2080
23. S.M. Brandstadter, and I. Ojima Tetrahedron Lett. 28 1987 613 616
24. J.-E. Dubois, and G. Axiotis Tetrahedron Lett. 25 1984 2143 2146
25. C. Gennari, I. Venturini, G. Gislon, and G. Schimperna Tetrahedron Lett. 28 1987 227 230
26. T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu Tetrahedron Lett. 32 1991 7563 7566
27. T. Fujisawa, M. Ichikawa, Y. Ukaji, and M. Shimizu Tetrahedron Lett. 34 1993 1307 1310
28. F. Lazzaro, M. Crucianelli, F. De Angelis, M. Frigerio, L. Malpezzi, A. Volonterio, and M. Zanda Tetrahedron: Asymmetry 15 2004 889 893
29. P. Bravo, S. Fustero, M. Guidetti, A. Volonterio, and M. Zanda J. Org. Chem. 64 1999 8731 8735
30. J.C. Adrian Jr., J.L. Barkin, R.J. Fox, J.E. Chick, A.D. Hunter, and R.A. Nicklow J. Org. Chem. 65 2000 6264 6267
31. E.M. Ferstl, H. Venkatesan, N.B. Ambhaikar, J.P. Snyder, and D.C. Liotta Synthesis 2002 2075 2083
32. M. Periasamy, G. Srinivas, G.V. Karunakar, and P. Bharathi Tetrahedron Lett. 40 1999 7577 7580
33. M. Periasamy, G. Srinivas, and S. Suresh Tetrahedron Lett. 42 2001 7123 7125
34. M. Periasamy, G. Srinivas, and P. Bharathi J. Org. Chem. 64 1999 4204 4205
35. Periasamy, M. Unpublished results.
36. M. Periasamy, and G. Srinivas Tetrahedron Lett. 43 2002 2785 2788
37. S. Suresh, and M. Periasamy Tetrahedron Lett. 45 2004 6291 6293
38. 2 = 0.0830. (Deposition number CCDC 265595.)
39. 2 = 0.1085. (Deposition number CCDC 265594.)
40. C.G. McCarty S. Patai Chemistry of the Carbon-Nitrogen Double Bond 1970 Wiley New York 364 372
41. D.Y. Curtin, E.J. Grubbs, and C.G. McCarty J. Am. Chem. Soc. 88 1966 2775 2786