Integrated reactions using addition to conjugated imines and iminium salts

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 69, Issue 10, 2011, Pages 1134-1144

  Hata, Shingo ^a   Shimizu, Makoto ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

imino ester; Alkoxycarbonyl iminium salt; Amino ketene silyl acetal; Dialkylaluminum chloride; Electrophilic amination; Iminomalonate; N alkylation; Umpolung

Indexed keywords

DIALKYLALUMINUM CHLORIDE; ELECTROPHILIC AMINATION; IMINIUM SALTS; IMINOMALONATE; KETENE SILYL ACETAL; N-ALKYLATION; UMPOLUNG;

ACETONITRILE; ADDITION REACTIONS; ALKYLATION; AMINES; CHLORINE COMPOUNDS; ESTERIFICATION; ESTERS;

AMINATION;

EID: 83055170850     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.69.1134     Document Type: Article

References (47)

1. (a) M. Shimizu, Pure Appl. Chem., 78, 1867(2006) ;
2. (b) M. Shimizu, I. Hachiya, I. Mizota, Chem. Commun., 2009, 874
3. M. Shimizu, Y. Niwa, Tetrahedron Lett., 42, 2829(2001)
4. Y. Niwa, M. Shimizu, J. Am. Chem. Soc., 125, 3720(2003)
5. (a) S. Mabic, A. A. Cordi, Tetrahedron., 57, 8861(2001) ;
6. (b) C. Palomo, M. Oiarbide, A. Landa, J. Org. Chem., 65, 41(2000):
7. (c) F. A. Davis, P. S. Portonove, R. E. Reddy, Y. Chiu, J. Org. Chem., 61, 440(1996)
8. M. Shimizu, Y. Niwa, T. Nagai, I. Hachiya, Heterocycles., 72, 127(2007)
9. (a) Y. Niwa, K. Takayama, M. Shimizu, Tetrahedron Lett., 42, 5473(2001) ;
10. (b) Y. Niwa, K. Takayama, M. Shimizu, Bull. Chem. Soc. Jpn., 75, 1819(2002)
11. E. Ciganek, Org. Reactions., 72, 1(2009)
12. (a) A. Armstrong, M. A. Atkin, S. Swallow, Tetrahedron Lett., 41, 2247(2000):
13. (b) D. Enders, C. Poiesz, R. Joseph, Tetrahedron: Asymmetry. 9, 3709(1998) ;
14. (c) J. Vidal, L. Guy, S. Steria, A. Collet., J. Org. Chem., 58, 4791(1993) ;
15. (d) S. Andreae, E. Schmitz, Synthesis., 1991, 327
16. (a) A. Armstrong, M. A. Atkin, S. Swallow, Tetrahedron Lett., 41, 2247(2000) ;
17. (b) D. Enders, C. Poiesz, R. Joseph, Tetrahedron: Asymmetry. 9, 3709(1998) ;
18. (c) J. Vidal, L. Guy, S. Stérin, A. Collet, J. Org. Chem., 58, 4791(1993):
19. (d) S. Andreae, E. Schmitz, Synthesis., 1991, 327
20. (a) G. Alvernhe, A. Laurent, Tetrahedron Lett., 13, 1007(1972) ;
21. (b) R. A. Hagopiaa, M. J. Therien, J. R. Murdoch, J. Am. Chem. Soc., 106, 5753(1984) ;
22. (c) H. Tsutsui, T. Ichikawa, K. Narasaka, Bull. Chem. Soc. Jpn., 72, 1869(1999)
23. (a) K. Oka, S. Hara, Tetrahedron Lett., 28, 2939(1977) ;
24. (b) A. K. Bose, M. Tsai, J. C. Kapur, Tetrahedron Lett., 15, 3547(1974)
25. J.-C. Fiaud, H. B. Kagan, Tetrahedron Lett., 12, 1019(1971)
26. (a) M. Shimizu, H. Itou, M. Miura, J. Am. Chem. Soc., 127, 3296(2005) ;
27. (b) T. Iwao, M. Shimizu, Heterocycles., 77, 767(2009) ;
28. (c) M. Shimizu, H. Itou, T. Iwao, Y. Umeda, Chem. Lett., 38, 73(2009) ;
29. (d) S. Hata, H. Koyama, M. Shimizu, unpublished results
30. W. Schroth, U. Jahn, J. Andersch, Synthesis., 1997, 573
31. H. Yun, Synlett., 2004. 1321. and references therein.
32. H. H. Mooiweer, E. C. Roots, H. Hiemstra, W. N. Speckamp, J. Org. Chem., 57, 6769(1992)
33. M. Okuda, H. Hioki, W. Miyagi, S. Ito, Tetrahedron Lett., 34, 6131(1993)
34. (a) M. Suginome, L. Uehlin, M. Murakami, J. Am. Chem. Soc., 126, 13196(2004) ;
35. (b) J. Yoshida, S. Suga, M. Watanabe, J. Am. Chem. Soc., 124, 14824(2002)
36. M. Shimizu, T. Kusunoki, M. Yoshida, K. Kondo, I. Mizota, Chem. Lett., 40, 351(2011)
37. J. S. Dicksteia, M. C. Kozlowaki, Chem. Soc. Rev., 37, 1167(2008)
38. (a) M. P. Bertrand, L. Feray, R. Nouguier, P. Perfetti, Synlett., 1999. 1148;
39. (b) K. Uneyama, F. Yan, S. Hirama, T. Katagiri, Tetrahedron Lett., 37, 2045(1996) ;
40. (c) Y. Yamamoto, W. Ito, Tetrahedron., 44, 5415(1988):
41. (d) M. R. P. van Vliet, J. T. B. H. Jastrzebski, W. J. Klaver, K. Goubitz, G. van Koten, Reel. Trav. Chim. Pays-Bos., 106, 132(1987):
42. (e) J.-C. Fiaud, H. B. Kagan, Tetrahedron Lett., 12, 1019(1971)
43. (a) P. J. De Clercp, Chem. Rev., 97, 1755(1997) ;
44. (b) J. Stubbe, J. K. Kozarich, Chem. Rev., 87, 1107(1987)
45. (a) Y. L. Bennari, S. Hanessian, Chem. Rev., 97, 3161(1997):
46. (b) K. Tomioka, Synthesis., 1990. 541;
47. (c) J. K. Whitesell, Chem. Rev., 89, 1581(1989)