Total regioselective transformation of aromatic aziridine 2-carboxamides into 2-aminoamides promoted by active manganese

Journal of Organic Chemistry

Volumn 75, Issue 7, 2010, Pages 2407-2410

  Concellón, José M ^a   Rodriguez Solla, Humberto ^a   Del Amo, Vicente ^a   Díaz, Pamela ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; MANGANESE; REGIOSELECTIVITY;

AMINOAMIDE; AZIRIDINES; CARBOXAMIDES; MORPHOLINES; ORGANOLITHIUM COMPOUNDS; REGIO-SELECTIVE;

KETONES;

2 AMINOAMIDE; AMIDE; AMINOKETONE; AROMATIC COMPOUND; AZIRIDINE DERIVATIVE; MANGANESE; MORPHOLINE DERIVATIVE; N 4 METHOXYPHENYLAZIRIDINE 2 CARBOXAMIDE; ORGANOLITHIUM COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; RING OPENING;

AZIRIDINES; CATALYSIS; CYCLIZATION; KETONES; LITHIUM COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MANGANESE; MOLECULAR STRUCTURE; MORPHOLINES; STEREOISOMERISM;

EID: 77950314220     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902708x     Document Type: Article

References (23)

1. Lindhorst, T. K, Essentials of Carbohydrate Chemistry and Biochemistry, 3rd ed.; Wiley-VCH: Weinheim, Germany, 2007.
2. (a) Hudlicky, T.; Reed, J. W. The Way of Synthesis: Evolution of Design and Methods for Natural Products, 1st ed.; Wiley-VCH: Weinheim, Germany, 2007.
3. (b) Bhat, S. V.; Nagasampagi, B. A.; Sivakumar, M. Chemistry of Natural Products, 1st ed.; Springer: Berlin, Germany, 2005.
4. Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013-3028.
5. (a) Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 2596-2599.
6. (b) Molander, G. A.; La Belle, B. E.; Hahn G. J. Org. Chem. 1986, 51, 5259.
7. (a) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 4437-4440.
8. (b) Reetz, M. T.; Lauterbach, E. H. Tetrahedron Lett. 1991, 32, 4477-4480.
9. Concellón, J. M,; Bardales, E.; Gómez, C. Tetrahedron Lett. 2003, 44, 5323-5326.
10. Concellón, J. M.; Bardales, E. Org. Lett. 2003, 5, 4783-4785.
11. Concellón, J. M.; Bernad, P. L.; Rodriguez-Solla, H.; Díaz, P. Adv. Synth. Catal. 2009, 351, 2178-2184.
12. Maguire, N. E.; McLaren, A. B.; Sweeney, J. B. Synlett 2003, 1898-1900.
13. (a) Pak, C. S.; Kim, T. H.; Ha, S. J. J. Org. Chem. 1998, 63, 10006-10010.
14. (b) Lee, G. H.; Youn, I. K.; Choi, E. B.; Lee, H. K.; Yon, G. H.; Yang, H. C.; Pak, C. S. Curr. Org. Chem. 2004, 8, 1263-1287.
15. (a) Molander, G. A.; Stengel, P. J. J Org. Chem. 1995, 60, 6660-6661.
16. (b) Molander, G. A.; Stengel, P. J. Tetrahedron 1997, 53, 8887-8912.
17. Kim, S.-.H.; Hanson, M. V.; Rieke, R. D. Tetrahedron Lett. 1996, 37, 2197-2200.
18. Wang, Y.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156-8157.
19. Martin, R.; Romea, P.; Tey, C.; Urpi, F.; Vilarrasa, J. Synlett 1997, 1414-1416.
20. Berkowitz, D. B.; Wu, B.; Li, H. Org. Lett, 2006, 8, 971-974.
21. Anderson, J. C.; Skerratt, S. J. Chem. Soc, Perkin Trans. 1 2002, 2871-2879.
22. (a) Peruncheralathan, S.; Henze, M.; Schneider, C Synlett 2007, 2289-2291.
23. (b) Yadav. J. S.; Reddy, B. V. S.; Vishweshwar Rao, K.; Saritha Raj, K.; Prasad, A. R. Synthesis 2002, 1061-1064.