Diastereoselectivity in addition of nitrile-stabilized carbanions to Schiff bases and in subsequent alkylation reactions

Tetrahedron

Volumn 61, Issue 24, 2005, Pages 5855-5865

  Viteva, L ^a   Gospodova, Tz ^a   Stefanovsky, Y ^a   Simova, S ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

Author keywords

Aldol addition; Alkylation; Diastereoselectivity; Nitrile stabilized carbanions; Schiff bases; Tandem reactions

Indexed keywords

ANION; AROMATIC COMPOUND; BENZYLCYANIDE; CARBON; CYANIDE; NITRILE; PROPIONITRILE; PROTON; SCHIFF BASE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYLATION; ARTICLE; CHIRALITY; LITHIATION; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 19744379176     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.04.010     Document Type: Article

References (49)

1. S. Arseniyadis, K.S. Kyler, and D.S. Watt Org. React. 1984 31
2. F.F. Fleming, and B.C. Shook Tetrahedron 58 2002 1 23
3. A.M. Baradel, J. Dreux, and R. Longeray Bull. Soc. Chim. Fr. 1970 255 258
4. G. Kyriakakou, M.C. Roux-Schmitt, and J. Seyden-Penne Tetrahedron 31 1975 1883 1888
5. R. Sauvetre, M.C. Roux-Schmitt, and J. Seyden-Penne Tetrahedron 34 1978 2135 2140
6. M. El-Bouz, M.C. Roux-Schmitt, and L. Wartsky J. Chem. Soc., Chem. Commun. 1979 779 780
7. M.C. Roux-Schmitt, L. Wartsky, and J. Seyden-Penne Tetrahedron 37 1981 1927 1934
8. M. Cossentini, and J. Seyden-Penne Synth. Commun. 15 1985 689 696
9. M. Cossentini, T. Strzalko, and J. Seyden-Penne Bull. Soc. Chim. Fr. 1987 531 534
10. A. Dobrev, C. Ivanov, A. Lattes, and M. Bon Bull. Soc. Chim. Fr. 1987 1084 1088
11. A.N. Kasatkin, R.Kh. Bictimirov, G.A. Tolstikov, and A.G. Nikonenko J. Org. Chem. USSR 26 1990 1037 1045
12. H. Hamana, and T. Sugasawa Chem. Lett. 1982 1401 1404
13. T. Kauffmann, H. Kieper, and H. Pieper Chem. Ber. 125 1992 899 905
14. K. Fuji Chem. Rev. 93 1993 2037 2066
15. L. Viteva, and Y. Stefanovsky Tetrahedron Lett. 30 1989 4565 4568
16. L. Viteva, and L. Gorrichon Mh. Chem. 126 1995 1001 1009
17. L. Viteva, Tz. Gospodova, Y. Stefanovsky, S. Angelova, and L. Gorrichon Tetrahedron 58 2002 3371 3378
18. Y. Stefanovsky, and L. Viteva Mh. Chem. 111 1980 1287 1298
19. Y. Stefanovsky, and L. Viteva Mh. Chem. 112 1981 125 128
20. Y. Stefanovsky, and L. Viteva Mh. Chem. 113 1982 181 190
21. Y. Stefanovsky, Tz. Gospodova, and L. Viteva Tetrahedron 42 1986 5355 5362
22. L. Viteva, and Y. Stefanovsky Tetrahedron Lett. 30 1989 4565 4568
23. L. Viteva, and Y. Stefanovsky J. Chem. Res. (S) 1990 232 233
24. L. Viteva, and Y. Stefanovsky Tetrahedron Lett. 31 1990 5649 5652
25. L.Z. Viteva, Tz.S. Gospodova, and Y.N. Stefanovsky Tetrahedron 50 1994 7193 7202
26. N.M. Mollov, and P.Ch. Petrova Commun. Inst. Org. Chem. Bulg. Acad. Sci. 1964 127 138
27. C. Ivanov, and V. Dryanska C. R. Acad. Bulg. Sci. 22 1969 423 426
28. V. Dryanska, and D. Tasheva Synth. Commun. 22 1992 63 71
29. L.Z. Viteva, Tz.S. Gospodova, and Y.N. Stefanovsky J. Chem. Res. (S) 2000 133 135
30. Y.N. Stefanovsky, and B.J. Kurtev C. R. Acad. Bulg. Sci. 22 1969 53 55
31. S.I. Novkova, M.K. Georgieva, Y.I. Binev, Ch.Ts. Petkov, and I.G. Binev J. Mol. Struct. (Teochem.) 636 2003 167 183
32. C.H. Heathcock The aldol addition reaction J.D. Morrison Asymmetric Synthesis Vol. 3 1984 Academic New York 111 212
33. P.R. Garlier, and K.M. Lo J. Org. Chem. 59 1994 4053 4055
34. P.R. Garlier, K.M. Lo, M.M.-C. Lo, and I.D. Williams Org. Chem. 60 1995 7511 7517
35. S. Simova Magn. Res. Chem. 36 1998 505 510
36. M.N. Paddon-Row, N.G. Rondon, and K.N. Houk J. Am. Chem. Soc. 104 1982 7162 7166
37. K.N. Houk, N.G. Rondon, Y.-D. Wu, M.N. Metzand, and M.N. Paddon-Row Tetrahedron 40 1984 2257 2274
38. I. Fleming, and J.J. Lewis J. Chem. Soc., Perkin Trans. 1 1992 3257 3266
39. I. Fleming, and J.J. Lewis J. Chem. Soc., Perkin Trans. 1 1992 3267 3276
40. R.A.N.C. Crump, I. Fleming, J.H.M. Hill, D. Parker, N.L. Reddy, and D. Waterson J. Chem. Soc., Perkin Trans. 1 1992 3277 3294
41. I. Fleming, and J.D. Kilbrun J. Chem. Soc., Perkin Trans. 1 1992 3295 3302
42. I. Fleming J. Chem. Soc., Perkin Trans. 1 1992 3303 3308
43. A. Alexakis, G.P. Trevitt, and G. Bernardinelli J. Am. Chem. Soc. 123 2001 4358 4359
44. G. Klopman J. Am. Chem. Soc. 90 1968 223 234
45. I.G. Binev, J.A. Tsenov, E.A. Velcheva, and I.N. Juchnovsky J. Mol. Struct. 344 1995 205 215
46. G. Albagnac, B. Brun, B. Calas, and L. Giral Bull. Soc. Chim. Fr. 1974 1469 1473
47. B. Deschamps, M.C. Roux-Schmitt, and L. Wartsky Tetrahedron Lett. 20 1979 1337 1380
48. T.B. McMahon, and P. Kebarle J. Am. Chem. Soc. 98 1976 3399 3406
49. T. Parella, F. Sanchez-Ferrando, and A. Virgili Magn. Res. Chem. 32 1994 343 347