Ruthenium-catalyzed addition of primary amides to alkynes: A stereoselective synthesis of secondary enamides

Synthesis

Volumn , Issue 13, 2009, Pages 2283-2288

  Gooßen, Lukas J ^a   Blanchot, Mathieu ^a   Salih, Kifah S M ^a   Gooßen, Käthe ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

Alkynes; Amides; Enamides; Hydroamidation; Ruthenium

Indexed keywords

ALKYNES; CATALYST SYSTEM; DOUBLE-BOND ISOMERIZATION; E-ISOMERS; ENAMIDES; HYDROAMIDATION; IN-SITU; PRIMARY AMIDES; STEREOSELECTIVE SYNTHESIS; TERMINAL ALKYNE; TRIETHYLAMINE; YTTERBIUM TRIFLATE;

ACETYLENE; BUTANE; ISOMERIZATION; ISOMERS; LIQUEFIED PETROLEUM GAS; MOLECULAR SIEVES; RUTHENIUM; SIEVES; STEREOCHEMISTRY; STEREOSELECTIVITY; SUGAR (SUCROSE); YTTERBIUM;

AMIDES;

1,1 DIMETHYL 3 [(Z)-2-PHENYLVINYL]UREA; 1,4 BIS(DICYCLOHEXYLPHOSPHINO)BUTANE; 2 ACETAMIDO N [(E) 2 PHENYLVINYL]ACETAMIDE; 2 ACETAMIDO N [(Z) 2 PHENYLVINYL]ACETAMIDE; 2 BROMO 4,5 DIMETHOXY N [(Z) 2 (4 METHOXYPHENYL)VINYL]BENZAMIDE; 2 CYANO N [(Z) 2 PHENYLVINYL]ACETAMIDE; 2 METHYL N [(E) 2 PHENYLVINYL]ACRYLAMIDE; 2 METHYL N [(Z) 2 PHENYLVINYL]ACRYLAMIDE; 3 NITRO N [(Z) 2 PHENYLVINYL]BENZAMIDE; ALKYNE; AMIDE; BIS(2 METHALLYL)(CYCLOOCTA 1,5 DIENE)RUTHENIUM II; ENAMIDE DERIVATIVE; ETHYL OXO[((E) 2 PHENYLVINYL)AMINO]ACETATE; N [(E) 2 (4 METHOXYPHENYL)VINYL]BENZAMIDE; N [(E) 3,3 CIMETHYLBUT 1 EN 1 YL]BENZAMIDE; N [(E) 4 PHENYLBUT 1 EN 1 YL]BENZAMIDE; N [(E) HEX 1 EN 1 YL]BENZAMIDE; N [(Z) 2 (4 FLUOROPHENYL)VINYL]BENZAMIDE; N [(Z) 2 (4 METHOXYPHENYL)VINYL]BENZAMIDE; N [(Z) 3,3 DIMETHYLBUT 1 EN 1 YL]BENZAMIDE; N [(Z) 4 PHENYLBUT 1 EN 1 YL]BENZAMIDE; N [(Z) 5 CHLOROPENT 1 EN 1 YL]BENZAMIDE; N [(Z) HEX 1 EN 1 YL]BENZAMIDE; RUTHENIUM; TRIETHYLAMINE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; YTTERBIUM TRIFLATE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMER; ISOMERIZATION;

EID: 67651092413     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216847     Document Type: Article

References (28)

1. Yet, L. Chem. Rev. 2003, 103, 4283.
2. For reviews, see: (a) Faulkner, D. J. Nat. Prod. Rep. 1999, 16, 155.
3. (b) Faulkner, D. J. Nat. Prod. Rep. 2000, 17, 7.
4. For traditional syntheses of enamides, see: (a) Dupau, P.; Le Gendre, P.; Bruneau, C.; Dixneuf, P. H. Synlett 1999, 1832.
5. (b) Wang, X.; Porco, J. A. Jr. J. Org. Chem. 2001, 66, 8215.
6. (c) Bayer, A.; Maier, M. E. Tetrahedron 2004, 60, 6665.
7. (d) Boeckman, R. K. Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250.
8. (e) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Org. Lett. 2001, 3, 2045.
9. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413.
10. (a) Gooßen, L. J.; Rauhaus, J. E.; Deng, G. Angew. Chem. Int. Ed. 2005, 44, 4042.
11. (b) Gooßen, L. J.; Arndt, M.; Blanchot, M.; Rudolphi, F.; Menges, F.; Niedner-Schatteburg, G. Adv. Synth. Catal. 2008, 350, 2701.
12. Gooßen, L. J.; Blanchot, M.; Brinkmann, C.; Gooßen, K.; Karch, R.; Rivas-Nass, A. J. Org. Chem. 2006, 71, 9506.
13. Gooßen, L. J.; Blanchot, M.; Salih, K. S. M.; Karch, R.; Rivas-Nass, A. Org. Lett. 2008, 10, 4497.
14. For related additions of other nucleophiles to alkynes, see: (a) Mitsudo, T.-A.; Hori, Y.; Watanabe, Y. J. Org. Chem. 1985, 50, 1566.
15. (b) Doucet, H.; Derrien, N.; Kabouche, Z.; Bruneau, C.; Dixneuf, P. H. J. Organomet. Chem. 1997, 551, 151.
16. (c) Gooßen, L. J.; Paetzold, J.; Koley, D. Chem. Commun. 2003, 706.
17. (d) Tokunaga, M.; Suzuki, T.; Koga, N.; Fukushima, T.; Horiuchi, A.; Wakatsuki, Y. J. Am. Chem. Soc. 2001, 123, 11917.
18. (e) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Org. Lett. 2001, 3, 735.
19. (f) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104.
20. (g) Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795.
21. Gooßen, L. J.; Salih, K. S. M.; Blanchot, M. Angew. Chem. Int. Ed. 2008, 47, 8492.
22. (a) Lin, J.-H. Phytochemistry 1989, 28, 621.
23. (b) Stefanuti, I.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 3735.
24. (c) Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955.
25. (a) Ghosh, S.; Datta, D. B.; Sen, N. Synth. Commun. 1987, 17, 299.
26. (b) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 411.
27. (c) Estévez, J. C.; Villaverde, M. C.; Estévez, R. J.; Seijas, J. A.; Castedo, L. Synth. Commun. 1990, 20, 503.
28. Overman, L. E.; Clizbe, L. A.; Freerks, R. L.; Marlowe, C. K. J. Am. Chem. Soc. 1981, 103, 2807.