Copper-catalyzed aminohalogenation using the 2-NsNCl2/2-NsNHNa combination as the nitrogen and halogen sources for the synthesis of anti-alkyl 3-chloro-2-(o-nitrobenzenesulfonamido)-3-arylpropionates

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2249-2252

  Li, Guigen ^a   Wei, Han Xun ^a   Kim, Sun Hee ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CHLORINE; CINNAMIC ACID DERIVATIVE; COPPER; NITROGEN; PROPIONIC ACID DERIVATIVE; SULFONAMIDE;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; METABOLISM; STEREOISOMERISM; SYNTHESIS;

AMINATION; AMINES; CATALYSIS; CHLORINE; CINNAMATES; COPPER; NITROGEN; PROPIONATES; STEREOISOMERISM; SULFONAMIDES;

EID: 0034720957     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000120b     Document Type: Article

References (17)

1. Kemp, J. E. G., In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 3, pp 471-513.
2. (a) Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1991, 113, 5863.
3. (b) Barton, D. H. R.; Britten-Kelley, M. R.; Ferreira, D. J. Chem. Soc., Perkin Trans. 1 1978, 1090.
4. (c) Driguez, H.; Vermes, J.-P.; Lessard, J. Can. J. Chem. 1978, 56, 119.
5. (d) Lessard, J.; Driguez, H.; Vermes, J.-P. Tetrahedron Lett. 1970, 4887.
6. (a) Daniher, F. A.; Butler, P. E. J. Org. Chem. 1968, 33, 4336.
7. (b) Daniher, F. A.; Butler, P. E. J. Org. Chem. 1968, 33, 2637.
8. (c) Daniher, F. A.; Melchior, M. T.; Butler, P. E. J. Chem. Soc., Chem. Commun. 1968, 931.
9. (d) Seden, T. P.; Turner, R. W. J. Chem. Soc. C 1968, 876.
10. Li, G.; Wei, H.-X.; Kim, S. H.; Neighbors, M. Org. Lett. 1999, 1, 385.
11. (a) Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
12. (b) Nelson, S. G.; Spencer, K. L. Angew. Chem., Int. Ed. 2000, 39, 1323
13. (c) Wipf, P.; Henninger, T. C. J. Org. Chem. 1997, 62, 1586.
14. (d) Miller, S. C.; Scanlan, T. S. J. Am. Chem. Soc. 1997, 119, 2301.
15. Li, G.; Kim, S. H.; Wei, H.-X. Tetrahedron Lett., submitted for publication.
16. 2/NsNHNa has been previously utilized as the nitrogen source to react with selenium for the formation of diimidoselenium compounds: Bruncko; M.; Khuong, T.-A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454.
17. 3): 1, δ 168.3, 147.4, 135.5, 134.1, 133.7, 133.0, 130.5, 129.4, 128.8, 127.6, 125.6, 63.1, 61.3, 52.8; 3, δ 168.4, 147.3, 139.3, 134.3, 133.5, 132.9, 132.4, 130.5, 129.4, 127.4, 125.6, 63.1, 61.1. 52.8, 21.2; 4, δ 168.5, 147.2, 135.7, 133.9, 6.5, 125.6, 61.6, 57.8, 52.6, 19.2; 6, δ 168.3, 147.3, 135.3, 134.2, 134.1, 133.7, 133.0, 130.3, 129.1, 128.9, 125.6, 62.9, 60.5, 52.9; 7, δ 168.3, 147.3, 134.8, 134.1, 133.7, 133.1, 131.9, 130.3, 129.4, 125.6, 123.5, 62.8, 60.5, 52.9; 8, δ 168.3, 165.4, 160.5, 147.4, 134.1, 133.7, 133.0, 131.5, 131.5, 130.4, 129.6, 129.5, 125.6, 116.0, 115.6, 63.0, 60.5, 52.9; 9, δ 167.2, 148.1, 147.5, 138.1, 134.0, 133.9, 133.8, 133.0, 130.4, 129.8, 125.7, 124.1, 123.0, 62.8, 60.6, 13.8.