Preparation of vinylogous 2-sulfonylindolines by the palladium-catalyzed cyclization of 1-sulfonyl-1,3-dienes with N-Cbz-o-iodoanilines

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5463-5464

  Back, Thomas G ^a   Bethell, Richard J ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1 SULFONYL 1,3 DIENE; 2 SULFONYLINDOLINE; ALKADIENE; ANILINE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032581672     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01111-3     Document Type: Article

References (20)

1. 1. (a) Heck, R.F. Acc. Chem. Res. 1979, 12, 146-151.
2. (b) Heck, R.F. Org. Reactions 1982, 27, 345-390.
3. (c) de Meijere, A.; Meyer, F.E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
4. (d) Cabri, W.; Candiani, I. Acc.Chem. Res. 1995, 28, 2-7.
5. 2. For recent reviews of palladium-catalyzed coupling reactions, see: (a) Tsuji, J. Palladium Reagents and Catalysts, Wiley, Chichester, 1995.
6. (b) Heck, R.F. Palladium Reagents in Organic Synthesis, Academic Press, New York, 1985.
7. (c) Trost, B.M.; Verhoeven, T.R. In Comprehensive Organometallic Chemistry, Wilkinson, G. (Ed.), Pergamon Press, Oxford, 1982, Volume 8, pp. 799-938.
8. 3. Simpkins, N.S. Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993.
9. 4. For examples of C-C bond formation via Pd-catalyzed coupling of other types of unsaturated sulfones, see (a) Jin, Z.; Fuchs, P.L. Tetrahedron Lett. 1996, 37, 5253-5256.
10. (b) Jin, Z.; Fuchs, P.L. Tetrahedron Lett. 1993, 34, 5205-5208.
11. (c) Lee, S.W.; Fuchs, P.L. Tetrahedron Lett. 1993, 34, 5209-5212.
12. (d) Trost, B.M.; Seoane, P.; Mignani, S.; Acemoglu, M. J. Am. Chem. Soc. 1989, 111, 7487-7500.
13. (e) Trost, B.M.; Grese, T.A.; Chan, D.M.T. J. Am. Chem. Soc. 1991, 113, 7350-7362.
14. (f) Trost, B.M.; Grese, T.A.; J. Am. Chem. Soc. 1991, 113, 7363-7372.
15. (e) Takayama, H.; Suzuki, T. J. Chem. Soc., Chem. Commun. 1988, 1044-1045.
16. (f) Harrington, P.J.; DiFiore, K.A. Tetrahedron Lett. 1987, 28, 495-498.
17. 5. The anilines 1 were prepared from the following known compounds by standard methods. o-iodoaniline: commercially available (Aldrich Co.); o-iodo-p-toluidine: Kajigaeshi, S.; Kakinami, T.; Yamasaki, H.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn. 1988, 61, 600-602; 4-amino-3-iodobenzoic acid: Hill, M.L.; Raphael, R.A. Tetrahedron Lett. 1986, 27, 1293-1296; 4-amino-3-iodophenol: Kvalnes, D.E. J. Am. Chem. Soc. 1934, 56, 667-670.
18. 5. The anilines 1 were prepared from the following known compounds by standard methods. o-iodoaniline: commercially available (Aldrich Co.); o-iodo-p-toluidine: Kajigaeshi, S.; Kakinami, T.; Yamasaki, H.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn. 1988, 61, 600-602; 4-amino-3-iodobenzoic acid: Hill, M.L.; Raphael, R.A. Tetrahedron Lett. 1986, 27, 1293-1296; 4-amino-3-iodophenol: Kvalnes, D.E. J. Am. Chem. Soc. 1934, 56, 667-670.
19. 5. The anilines 1 were prepared from the following known compounds by standard methods. o-iodoaniline: commercially available (Aldrich Co.); o-iodo-p-toluidine: Kajigaeshi, S.; Kakinami, T.; Yamasaki, H.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn. 1988, 61, 600-602; 4-amino-3-iodobenzoic acid: Hill, M.L.; Raphael, R.A. Tetrahedron Lett. 1986, 27, 1293-1296; 4-amino-3-iodophenol: Kvalnes, D.E. J. Am. Chem. Soc. 1934, 56, 667-670.
20. 6. (E)-1-(p-Toluenesulfonyl)-1,3-butadiene, (E,E)-1-(p-toluenesulfonyl)-1,3-pentadiene and 2-methyl-1-(p-toluenesulfonyl)-1,3-butadiene (1:1 E,Z mixture) were prepared by the method of: Barluenga, J.; Martinez-Gallo, J.M.; Nájera, C.; Fañanás, F.J.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1987, 2605-2609.