α-Nitrogenated organolithium compounds from N-(tosylmethyl)amides

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 491-492

  Alonso, Diego A ^a   Alonso, Emma ^a   Nájera, Carmen ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002623684     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6111     Document Type: Article

References (20)

1. (a) Morton, J.; Rahim, A.; Walker, E. R. H. Tetrahedron Lett. 1982, 23, 4123.
2. (b) Pearson, W. H.; Lindbeck, A. C.; Kampf, J. W. J. Am. Chem. Soc. 1993, 115, 2622.
3. (a) Brown, D. S.; Hansson, T.; Ley, S. V. Synlett 1990, 48.
4. (b) Brown, D. S.; Charreau, P.; Hansson, T.; Ley, S. V. Tetrahedron 1991, 47, 1311.
5. (a) Brown, D. S.; Charreau, P.; Ley, S. V. Synlett 1990, 749.
6. (b) Basak, A.; Khamrai, U. K. Tetrahedron Lett. 1996, 37, 2475.
7. For the last paper on this topic from our laboratory, see: Alonso, D. A.; Falvello, L. R.; Mancheño, B.; Nájera, C.; Tomás, M. J. Org. Chem. 1996, 61, 5004.
8. Seebach, D. Angew. Chem. Int. Ed. Engl. 1979, 18, 239.
9. To our best knowledge, only one example on the lithiation of a α-amido sulfone and the reaction with methyl iodide has been recently described (reference 1b).
10. (a) Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306.
11. (b) Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356.
12. (a) Guijarro, D.; Yus, M. Tetrahedron Lett. 1994, 35, 2965.
13. (b) Alonso, E.; Guijarro, D.; Yus, M. Tetrahedron 1995, 51, 2699.
14. (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398.
15. (b) For a review, see: Yus, M. Chem. Soc. Rev., 1996, 155.
16. 2- synthon by arene catalysed lithiation under Barbier-type conditions (reference 11). For other methodologies to prepare α-nitrogenated organolithium compounds see literature cited in reference 11.
17. Guijarro, A.; Ortiz, J.; Yus, M. Tetrahedron Lett. 1996, 37, 5597.
18. (a) Engberts, J. B. F. N.; Strating, J. Recl. Trav. Chim. Pays-Bas 1964, 83, 733.
19. (b) Olijnsma, T.; Engberts, J. B. F. N.; Strating, J. Recl. Trav. Chim. Pays-Bas 1967, 86, 463.
20. Harris, A. R.; Mason, T. J.; Hanna, G. R. J. Chem. Res. (S) 1990, 218.