Copper(I)-catalyzed addition of grignard reagents to in situ-derived N -sulfonyl azoalkenes: An umpolung alkylation procedure applicable to the formation of up to three contiguous quaternary centers

Journal of the American Chemical Society

Volumn 132, Issue 13, 2010, Pages 4546-4547

  Hatcher, John M ^a   Coltart, Don M ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENOLATES; GRIGNARD REAGENT; IN-SITU; QUATERNARY CENTERS; SULFONYL HYDRAZONES; UMPOLUNG;

ALKYLATION; KETONES;

HYDROCARBONS;

ALKENE DERIVATIVE; COPPER; GRIGNARD REAGENT;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION; PROTEIN QUATERNARY STRUCTURE;

ALKENES; ALKYLATION; AZO COMPOUNDS; CATALYSIS; COPPER; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 77950844004     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja100932q     Document Type: Article

References (25)

1. For example, see: Berger, E. C. and Tunge, J. A. Org. Lett. 2004, 6, 2603
2. Berger, E. C. and Tunge, J. A. Org. Lett. 2004, 6, 4113
3. Behenna, D. C. and Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 15044
4. Doyle, A. G. and Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 62
5. Trost, B. M. and Xu, J. J. Am. Chem. Soc. 2005, 127, 17180
6. Graening, T. and Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 17192
7. Zheng, W.-H., Zheng, B.-H., Zhang, Y., and Hou, X.-L. J. Am. Chem. Soc. 2007, 129, 7718
8. Weix, D. J. and Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 7720
9. For ketones, see: Lundin, P. M., Esquivias, J., and Fu, G. C. Angew. Chem., Int. Ed. 2009, 48, 154
10. Malosh, C. F. and Ready, J. M. J. Am. Chem. Soc. 2004, 126, 10240
11. For carboxylate derivatives, see: Brand, G. J., Studte, C., and Breit, B. Org. Lett. 2009, 11, 4668
12. Studte, C. and Breit, B. Angew. Chem., Int. Ed. 2008, 47, 5451
13. Dai, X., Strotman, N. A., and Fu, G. C. J. Am. Chem. Soc. 2008, 130, 3302
14. Fischer, C. and Fu, G. C. J. Am. Chem. Soc. 2005, 127, 4594
15. Sacks, C. E. and Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372
16. 2CuLi add to preformed tosylazocyclohex-1-ene to give α-methyl- and α- t -Bu-tosylcyclohexanone, respectively (see ref 3).
17. Lipshutz, B. H. In Organometallics in Synthesis, 1 st ed.; Schlosser, M., Ed.; Wiley: Chichester, U.K., 1994; p 339.
18. See the Supporting Information for details.
19. The use of EtMgBr alone did not lead to product formation.
20. Rosini, G. and Baccolini, G. J. Org. Chem. 1974, 39, 826
21. Schlessinger, R. H. and Schultz, J. A. J. Org. Chem. 1983, 48, 407
22. Snowden, R. L., Brauchli, R., and Sonnay, P. Helv. Chim. Acta 1989, 72, 570
23. Tanaka, M. and Sakai, K. Tetrahedron Lett. 1991, 32, 5581
24. Kitano, Y., Fukuda, J., Chiba, K., and Tada, M. J. Chem. Soc., Perkin Trans. 1 1996, 829
25. Lange, G. L., Furlan, L., and MacKinnon, M. C. Tetrahedron Lett. 1998, 39, 5489