Sequential synthesis of (E)-α,β-unsaturated primary amides with complete stereoselectivity

Journal of Organic Chemistry

Volumn 75, Issue 10, 2010, Pages 3451-3453

  Concellón, José M ^a   Rodríguez Solla, Humberto ^a   Concellón, Carmen ^a   Simal, Carmen ^a   Alvaredo, Noemí ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROACETAMIDES; ENOLATES; GOOD YIELD; PRIMARY AMIDES; SEQUENTIAL REACTION; SEQUENTIAL SYNTHESIS; STEREOSELECTIVE SYNTHESIS;

ALDEHYDES; AMIDES; SAMARIUM; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

AMIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77952505554     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100320j     Document Type: Article

References (32)

1. For reviews of dianions of carboxylic acids, see: Petragnani, N.; Yonashiro, M. Synthesis 1982, 521-578
2. Thompson, C. M.; Green, D. L. C. Tetrahedron 1991, 47, 4223-4285
3. Concellón, J. M.; Concellón, C. J. Org. Chem. 2006, 71, 4428-4432
4. Concellón, J. M.; Concellón, C. J. Org. Chem. 2006, 71, 1728-1731
5. 2: Soderquist, J. A. Aldrichimica Acta 1991, 24, 15-23
6. Molander, G. A. Chem. Rev. 1992, 92, 29-68
7. Molander, G. A. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 251-282.
8. Molander, G. A. In Organic Reactions; Paquette, L. A., Ed.; John Wiley: New York, 1994; pp 211-367.
9. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338
10. Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354
11. Krief, A.; Laval, A. M. Chem. Rev. 1999, 99, 745-777
12. Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751
13. Kagan, H. B. Tetrahedron 2003, 59, 10351-10372
14. Concellón, J. M.; Rodríguez-Solla, H. Chem. Soc. Rev. 2004, 33, 599-609
15. Jung, D. Y.; Kim, Y. H. Synlett 2005, 3019-3032
16. Concellón, J. M.; Rodríguez-Solla, H. Eur. J. Org. Chem. 2006, 1613-1625
17. Gopalaiah, K.; Kagan, H. B. New J. Chem. 2008, 32, 607-637
18. Nicolaou, K. C.; Ellery, S. P.; Chen, J. S. Angew. Chem., Int. Ed. 2009, 48, 7140-7165
19. 2, see
20. Concellón, J. M.; Rodríguez-Solla, H.; Huerta, M.; Pérez-Andrés, J. A. Eur. J. Org. Chem. 2002, 1839-1847
21. When aromatic aldehydes were employed as starting materials, products derived from their pinacol coupling were isolated instead of the corresponding α,β-unsaturated amides 4.
22. For recent revisions on Samarium-enolates, see: Rudkin, I. M.; Miller, L. C.; Procter, D. J. Organomet. Chem. 2008, 34, 19-45
23. Procter, D. J.; Flowers, R. A., II; Skrydstrup, T. Organic Synthesis Using Samarium Diiodide: A Practical Guide; RSC Publishing: Cambridge, 2010.
24. Concellón, J. M.; Pérez-Andrés, J. A.; Rodríguez-Solla, H. Angew. Chem., Int. Ed. 2000, 39, 2773-2775
25. Concellón, J. M.; Pérez-Andrés, J. A.; Rodríguez-Solla, H. Chem.-Eur. J. 2001, 7, 3062-3068
26. 2
27. Molander, G. A.; Etter, J. B.; Zinke, P. W. J. Am. Chem. Soc. 1987, 109, 453-463
28. Urban, D.; Skrydstrup, T.; Beau, J. M. J. Org. Chem. 1998, 63, 2507-2516
29. Prasad, E.; Flowers, R. A., II J. Am. Chem. Soc. 2002, 124, 6357-6381
30. Enemrke, R. J.; Larsen, J.; Hjollund, G. H.; Skrydstrup, T.; Daasbjerg, K. Organometallics 2005, 24, 1252-1262
31. Davis, T. A.; Chopade, P. R.; Hilmersson, G.; Flowers, R. A. Org. Lett. 2005, 7, 119-122
32. For a discussion of the highly oxophilic character of Sm(III) species, see: Molander, G. A. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Schreiber, S. L., Eds.; Pergamon: Cambridge, 1991; Vol. 1, p 252.