Chemoselective activation strategies of amidic carbonyls towards nucleophilic reagents

Australian Journal of Chemistry

Volumn 66, Issue 5, 2013, Pages 507-510

  Pace, Vittorio ^a   Holzer, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOSELECTIVE; NUCLEOPHILIC REAGENT; WEINREB AMIDES;

CHEMICAL COMPOUNDS;

AMIDES;

EID: 84878094671     PISSN: 00049425     EISSN: 14450038     Source Type: Journal    
DOI: 10.1071/CH13042     Document Type: Article

References (22)

1. N. A. Afagh, A. K. Yudin, Angew. Chem. Int. Ed. 2010, 49, 262. doi:10.1002/ANIE.200901317
2. (a V. Grignard, C. R. Hebd. Seances Acad. Sci. 1900, 130, 1322.
3. (b For a historical perspective, see: H. B. Kagan, Angew. Chem. Int. Ed. 2012, 51, 7376. doi:10.1002/ANIE.201201849
4. D. Seebach, Angew. Chem. Int. Ed. 2011, 50, 96. doi:10.1002/ANIE. 201003823
5. (a S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815. doi:10.1016/S0040-4039(01)91316-4
6. (b For a review, see: S. Balasubramaniam, I. S. Aidhen, Synthesis 2008, 3707.
7. (c For a recent chemoselective application of Weinreb amides, see: V. Pace, W. Holzer, G. Verniest, A. R. Alcántara, N. De Kimpe, Adv. Synth. Catal. 2013, 355, 919. doi:10.1002/ADSC.201201043
8. K. Shirokane, Y. Kurosaki, T. Sato, N. Chida, Angew. Chem. Int. Ed. 2010, 49, 6369. doi:10.1002/ANIE.201001127
9. Y. Yanagita, H. Nakamura, K. Shirokane, Y. Kurosaki, T. Sato, N. Chida, Chem.-Eur. J. 2013, 19, 678. doi:10.1002/CHEM. 201202639
10. (a G. Vincent, R. Guillot, C. Kouklovsky, Angew. Chem. Int. Ed. 2011, 50, 1350. doi:10.1002/ANIE.201006590
11. (b For other examples of sequential nucleophilic additions to amidic carbonyls, see: G. Bélanger, G. O'Brien, R. Larouche-Gauthier, Org. Lett. 2011, 13, 4268. doi:10.1021/OL201616K
12. (c J. W. Medley, M. Movassaghi, Angew. Chem. Int. Ed. 2012, 51, 4572. doi:10.1002/ANIE.201200387
13. Y. Oda, T. Sato, N. Chida, Org. Lett. 2012, 14, 950. doi:10.1021/ OL3000316
14. J. T. Spletstoser, J. M. White, A. R. Tunoori, G. I. Georg, J. Am. Chem. Soc. 2007, 129, 3408. doi:10.1021/JA066362\+
15. A. B. Charette, M. Grenon, Can. J. Chem. 2001, 79, 1694. doi:10.1139/V01-150
16. G. Barbe, A. B. Charette, J. Am. Chem. Soc. 2008, 130, 18. doi:10.1021/JA077463Q
17. G. Pelletier, W. S. Bechara, A. B. Charette, J. Am. Chem. Soc. 2010, 132, 12817. doi:10.1021/JA105194S
18. (a W. S. Bechara, G. Pelletier, A. B. Charette, Nat. Chem. 2012, 4, 228. doi:10.1038/NCHEM.1268
19. (b After the publication of this work, an analogous approach based on organocerium chemistry was reported by Huang's group: K.-J. Xiao, A.-E. Wang, Y.-H. Huang, P.-Q. Huang, Asian. J. Org. Chem. 2012, 1, 130.
20. K.-J. Xiao, J.-M. Luo, K.-Y. Ye, Y. Wang, P.-Q. Huang, Angew. Chem. Int. Ed. 2010, 49, 3037. doi:10.1002/ANIE.201000652
21. K.-J. Xiao, Y. Wang, K.-Y. Ye, P.-Q. Huang, Chem.-Eur. J. 2010, 16, 12792. doi:10.1002/CHEM.201002054
22. K.-J. Xiao, A.-E. Wang, P.-Q. Huang, Angew. Chem. Int. Ed. 2012, 51, 8314. doi:10.1002/ANIE.201204098