The first catalytic Mannich-type reaction of N-alkoxycarbonylamino sulfones with silyl enolates

Advanced Synthesis and Catalysis

Volumn 348, Issue 15, 2006, Pages 2080-2084

  Ollevier, Thierry ^a   Nadeau, Etienne ^a   Eguillon, Jean Christophe ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

Bismuth; Green chemistry; Mannich bases; Mannich reaction; N alkoxycarbonylamino sulfones; Silyl enolates

Indexed keywords

EID: 33750000033     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606222     Document Type: Article

References (50)

1. For reviews of catalytic Mannich-type reactions: a) S. Kobayashi, M. Ueno, Comprehensive Asymmetric Catalysis, Supplement, Springer, Berlin, 2004, 1, 143-150;
2. b) A. Córdova, Acc. Chem. Res. 2004, 37, 102-112;
3. c) M. Arend, B. Westermann, N. Risch, Angew. Chem. Int. Ed. 1998, 37, 1044-1070;
4. d) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.-L Lam, Chem. Rev. 2002, 102, 2227-2302;
5. e) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094.
6. For reviews of multicomponent reactions: a) J. Zhu, H. Bienaymé (Eds.), Multicomponent Reactions, Wiley-VCH, Weinheim, 2005;
7. b) M. Syamala, Org. Prep. Proc. Int. 2005, 37, 103-171.
8. For recent examples of multicomponent reactions: c) S. Kobayashi, S. Iwamoto, S. Nagayama, Synlett 1997, 1099-1101;
9. d) T. Akiyama, J. Takaya, H. Kagoshima, Synlett 1999, 1426-1428;
10. e) S. Iimura, D. Nobutou, K. Manabe, S. Kobayashi, Chem. Commun. 2003, 1644-1645.
11. a) S. Kobayashi, M. Araki, H. Ishitani, S. Nagayama, I. Hachiya, Synlett 1995, 233-234;
12. b) S. Kobayashi, M. Araki, M. Yasuda, Tetrahedron Lett. 1995, 36, 5773-5776;
13. c) S. Kobayashi, T. Busujima, S. Nagayama, Synlett 1999, 545-546;
14. d) S. Kobayashi, M. Moriwaki, R. Akiyama, S. Suzuki, I. Hachiya, Tetrahedron Lett. 1996, 37, 7783-7786.
15. a) H. Suzuki, Y. Matano (Eds), Organobismuth Chemistry, Elsevier, Amsterdam, 2001;
16. b) H. Gaspard-Iloughmane, C. Le Roux, Eur. J. Org. Chem. 2004, 2517-2532;
17. c) N. M. Leonard, L. C. Wieland, R. S. Mohan, Tetrahedron 2002, 58, 8373-8397.
18. a) C. Ogawa, S. Azoulay, S. Kobayashi, Heterocycles 2005, 66, 201-206;
19. b) T. Ollevier, G. Lavie-Compin, Tetrahedron Lett. 2004, 45, 49-52;
20. c) T. Ollevier, G. Lavie-Compin, Tetrahedron Lett. 2002, 43, 7891-7893.
21. a) T. Ollevier, V. Desyroy, B. Debailleul, S. Vaur, Eur. J. Org. Chem. 2005, 4971-4973;
22. b) S. Kobayashi, T. Ogino, H. Shimizu, S. Ishikawa, T. Hamada, K. Manabe, Org. Lett. 2005, 7, 4729-4731;
23. c) C. Le Roux, L. Ciliberti, H. Laurent-Robert, A. Laporterie, J. Dubac, Synlett 1998, 1249-1251.
24. a) N. M. Leonard, M. C. Oswald, D. A. Freiberg, B. A. Nattier, R. C. Smith, R. S. Mohan, J. Org. Chem. 2002, 67, 5202-5207;
25. b) M. D. Carrigan, D. Sarapa, R. C. Smith, L. C. Wieland, R. S. Mohan, J. Org. Chem. 2002, 67, 1027-1030.
26. a) C. Le Roux, J. Dubac, Synlett 2002, 181-200;
27. b) J. R. Desmurs, M. Labrouillère, C. Le Roux, H. Gaspard, A. Laporterie, J. Dubac, Tetrahedron Lett. 1997, 38, 8871-8874;
28. c) S. Répichet, C. Le Roux, J. Dubac, J. R. Desmurs, Eur. J. Org. Chem. 1998, 2743-2746.
29. a) T. Ollevier, V. Desyroy, M. Asim, M.-C. Brochu, Synlett 2004, 2794-2796;
30. b) T. Ollevier, T. M. Mwene-Mbeja, Tetrahedron Lett. 2006, 47, 4051-4055;
31. c) B. Sreedhar, V. Swapna, C. Sridhar, Synth. Commun. 2004, 34, 1433-1440.
32. a) T. Ollevier, T. Ba, Tetrahedron Lett. 2003, 44, 9003-9005;
33. b) B. Leroy, I. E. Markó, Org. Lett. 2002, 4, 47-50.
34. a) S. Répichet, A. Zwick, L. Vendier, C. Le Roux, J. Dubac, Tetrahedron Lett. 2002, 43, 993-995;
35. b) M. Labrouillère, C. Le Roux, H. Gaspard, A. Laporterie, J. Dubac, J. R. Desmurs, Tetrahedron Lett. 1999, 40, 285-286;
36. c) M. Peyronneau, C. Arrondo, L. Vendier, N. Roques, C. Le Roux, J. Mol. Cat A 2004, 211, 89-91;
37. [11a]
38. a) T. Ollevier, E. Nadeau, Synlett 2006, 219-222;
39. b) T. Ollevier, E. Nadeau, J. Org. Chem. 2004, 69, 9292-9295.
40. For a recent review of N-alkoxycarbonylamino sulfones as precursors of N-alkoxycarbonyl iminium derivatives: M. Petrini, Chem. Rev. 2005, 105, 3949-3977.
41. a) J. B. F. N. Engberts, J. Strating, Reel. Trav. Chim. 1965, 84, 942-950;
42. b) T. Mecozzi, M. Petrini, J. Org. Chem. 1999, 64, 8970-8972.
43. a) N. Giri, M. Petrini, R. Profeta, J. Org. Chem. 2004, 69, 7303-7308;
44. b) T. Mecozzi, M. Petrini, R. Profeta, J. Org. Chem. 2001, 66, 8264-8267;
45. c) C. Palomo, M. Oiarbide, M. C. González-Rego, A. K. Sharma, J. M. Garciá, A. González, C. Landa, A. Linden, Angew. Chem. Int. Ed. 2000, 39, 1063-1065.
46. a) M. Petrini, E. Torregiani, Tetrahedron Lett. 2005, 46, 5999-6003;
47. b) D. Enders, S. Oberbörsch, Synlett 2002, 471-473;
48. c) A. Giardinà, T. Mecozzi, M. Petrini, J. Org. Chem. 2000, 65, 8277-8282.
49. Various β-amino ketones derivatives were found very effective as bioactive compounds: H. Buschmann, C. Puetz, D. Enders, S. Oberboersch, US Patent 0096361 A1, 2005.
50. A related strategy has been disclosed in solid-phase synthesis: S. Schunk, D. Enders, Org. Lett. 2001, 3, 3177-3180.