Aminomethylation of Michael acceptors: Complementary radical and polar approaches mediated by dialkylzincs

Chemistry - A European Journal

Volumn 18, Issue 11, 2012, Pages 3241-3247

  Maury, Julien ^a   Mouysset, Dominique ^a   Feray, Laurence ^a   Marque, Sylvain R A ^a   Siri, Didier ^a   Bertrand, Michèle P ^a  

^a AIX MARSEILLE UNIV   (France)

Author keywords

aminomethylation; dialkylzincs; ESR experiments; radical reactions; theoretical calculations; zinc

Indexed keywords

AMINOMETHYLATION; COMPLEMENTARY METHODS; DIALKYLZINCS; DIETHYL FUMARATE; FUNCTIONALIZED; MICHAEL ACCEPTORS; PYRROLIZIDINES; RADICAL ADDITION; RADICAL MECHANISM; RADICAL PRECURSOR; RADICAL REACTIONS; THEORETICAL CALCULATIONS; TRANSMETALATION;

EXPERIMENTS; ISOMERS; REACTION KINETICS; ZINC;

METHYLATION;

EID: 84857838629     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102366     Document Type: Article

References (44)

1. C. Chatgilialoglu, Chem. Eur. J. 2008, 14, 2310-2320
2. C. Chatgilialoglu, V. I. Timokhin, Adv. Organomet. Chem. 2008, 57, 117-181
3. S. Kim, S. Kim, Bull. Chem. Soc. Jpn. 2007, 80, 809-822
4. K. C. Majumdar, P. Debnath, Tetrahedron 2008, 64, 9799-9820
5. C. Ollivier, P. Renaud, Chem. Rev. 2001, 101, 3415-3434
6. V. Darmency, P. Renaud, Top. Curr. Chem. 2006, 263, 71-106
7. A. P. Schaffner, P. Renaud, Eur. J. Org. Chem. 2004, 2291-2298
8. B. Quiclet-Sire, S. Zard, Chem. Eur. J. 2006, 12, 6002-6016
9. A. Studer, Chem. Soc. Rev. 2004, 33, 267-273
10. P. A. Baguley, J. C. Walton, Angew. Chem. 1998, 110, 3272-3283
11. Angew. Chem. Int. Ed. 1998, 37, 3072-3082.
12. L. Feray, M. P. Bertrand, Eur. J. Org. Chem. 2008, 3164-3170.
13. S. Bazin, L. Feray, M. P. Bertrand, Chimia 2006, 60, 260-265
14. T. Akindele, K.-I. Yamada, K. Tomioka, Acc. Chem. Res. 2009, 42, 345-355.
15. M. P. Bertrand, L. Feray, R. Nouguier, P. Perfetti, Synlett 1999, 1148-1150
16. M. P. Bertrand, L. Feray, R. Nouguier, P. Perfetti, J. Org. Chem. 1999, 64, 9189-9193
17. M. P. Bertrand, S. Coantic, L. Feray, R. Nouguier, P. Perfetti, Tetrahedron 2000, 56, 3951-3961
18. S. Bazin, L. Feray, D. Siri, J.-V. Naubron, M. P. Bertrand, Chem. Commun. 2002, 2506-2507
19. F. Cougnon, S. Bazin, L. Feray, M. P. Bertrand, Tetrahedron 2007, 63, 11959-11964
20. S. Bazin, L. Feray, N. Vanthuyne, D. Siri, M. P. Bertrand, Tetrahedron 2007, 63, 77-85
21. J. Maury, L. Feray, S. Bazin, J.-L. Clément, S. R. A. Marque, D. Siri, M. P. Bertrand, Chem. Eur. J. 2011, 17, 1586-1595
22. J. Maury, L. Feray, M. P. Bertrand, Org. Lett. 2011, 13, 1884-1887.
23. K.-I. Yamada, M. Nakano, M. Maekawa, T. Akindele, K. Tomioka, Org. Lett. 2008, 10, 3805-3808
24. K.-I. Yamada, H. Umeki, M. Maekawa, Y. Yamamoto, T. Akindele, M. Nakano, K. Tomioka, Tetrahedron 2008, 64, 7258-7265
25. K.-I. Yamada, M. Maekawa, T. Akindele, Y. Yamamoto, M. Nakano, K. Tomioka, Tetrahedron 2009, 65, 903-908
26. A. Pérez-Luna, C. Botuha, F. Ferreira, F. Chemla, Chem. Eur. J. 2008, 14, 8784-8788
27. S. Giboulot, A. Pérez-Luna, C. Botuha, F. Ferreira, F. Chemla, Tetrahedron Lett. 2008, 49, 3963-3966
28. F. Chemla, F. Dulong, F. Ferreira, M. P. Nüllen, A. Pérez-Luna, Synthesis 2011, 1347-1360
29. T. Cohen, H. Gibney, R. Ivanov, E. A.-H. Yeh, I. Marek, D. P. Curran, J. Am. Chem. Soc. 2007, 129, 15405-15409
30. Z. Chen, Y.-X. Zhang, Y. An, X.-L. Song, Y.-H. Wang, L.-L. Zhu, L. Guo, Eur. J. Org. Chem. 2009, 5146-5152.
31. J.-Y. Liu, Y.-J. Jang, W.-W. Lin, J.-T. Liu, C.-F. Yao, J. Org. Chem. 2003, 68, 4030-4038.
32. J. Maury, L. Feray, P. Perfetti, M. P. Bertrand, Org. Lett. 2010, 12, 3590-3593.
33. B. Quiclet-Sire, G. Revol, S. Z. Zard, Org. Lett. 2009, 11, 3554-3557
34. B. Quiclet-Sire, S. Z. Zard, Org. Lett. 2008, 10, 3279-3282.
35. U. C. Yoon, D. U. Kim, C. W. Lee, Y. S. Choi, Y.-J. Lee, H. L. Ammon, P. S. Mariano, J. Am. Chem. Soc. 1995, 117, 2698-2710
36. E. F. Campbell, A. K. Park, W. A. Kinney, R. W. Fengl, L. S. Liebeskind, J. Org. Chem. 1995, 60, 1470-1472
37. J.-M. Receveur, J. Guiramand, M. Récasens, M.-L. Roumestant, P. Viallefont, J. Martinez, Bioorg. Med. Chem. Lett. 1998, 8, 127-132.
38. P. Knochel, T.-S. Chou, C. Jubert, D. Rajagopal, J. Org. Chem. 1993, 58, 588-599.
39. R. P. Iyer, D. Yu, N.-H. Ho, S. Agrawal, Synth. Commun. 1995, 25, 2739-2749
40. A. B. Charette, A. Beauchemin, S. Francoeur, J. Am. Chem. Soc. 2001, 123, 8139-8140. See: Supporting Information.
41. S. Bazin, L. Feray, N. Vanthuyne, M. P. Bertrand, Tetrahedron 2005, 61, 4261-4274
42. S. Lai, C. K. Zercher, J. P. Jasinski, S. N. Reid, R. J. Staples, Org. Lett. 2001, 3, 4169-4171.
43. A. B. Charette, A. Beauchemin, J.-F. Marcoux, J. Am. Chem. Soc. 1998, 120, 5114-5115.
44. This transmetalation was assumed to involve the formation of radicals, see:, P. Knochel, Synlett 1995, 393-403. This was indirectly confirmed by ESR experiments performed in the presence of 3, diethylzinc, CuI, and TTBNB. The same spectrum as in Figure 1 was observed for these reactions.