Novel synthesis of azepine derivatives via copper-mediated cyclization of 2-Aza-hepta-2,4-dien-6-ynyl anions. Intramolecular addition of organocopper centers to the C-C triple bond

Organic Letters

Volumn 9, Issue 6, 2007, Pages 1049-1052

  Lyaskovskyy, Volodymyr ^a   Bergander, Klaus ^a   Fröhlich, Roland ^a   Würthwein, Ernst Ulrich ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ANION; AZEPINE DERIVATIVE; CARBON; COPPER; ORGANOMETALLIC COMPOUND; PROTON;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKYNES; ANIONS; AZEPINES; CARBON; CATALYSIS; COPPER; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; ORGANOMETALLIC COMPOUNDS; PROTONS; STEREOISOMERISM;

EID: 33947584629     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol063081y     Document Type: Article

References (19)

1. See, for example: (a) Smalley, R. K. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon Press: Bristol, 1984; Vol. 7, pp 545-546.
2. (b) Meigh, J.-P. K. In Science of Synthesis; Weinreb, S. M., Ed.; Thieme: Stuttgart, New York, 2004; Vol. 17, pp 829-830 and references therein.
3. (a) Surman, M. D.; Hutchings, R. H. In Science of Synthesis; Weinreb, S. M., Ed.; Thieme: Stuttgart, New York, 2004; Vol. 17, pp 749-823.
4. (b) Meigh, J.-P. K. In Science of Synthesis; Weinreb, S. M., Ed.; Thieme: Stuttgart, New York, 2004; Vol. 17, pp 825-927.
5. (c) Smalley, R. K. In Methods of Organic Chemistry (Houben-Weyl); Schaumann, E., Ed. Thieme: Stuttgart, New York, 1998; Vol. E9d, pp 108-199.
6. (d) Smalley R. K. In Methods of Organic Chemistry (Houben-Weyl); Schaumann, E. Ed.; Thieme: Stuttgart, New York, 1998; Vol. E9d, pp 207-292.
7. (e) Smalley, R. K. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon Press: Bristol, 1984; Vol. 7, pp 491-545.
8. Sagar, P.; Fröhlich, R.; Würthwein, E.-U. Angew. Chem. 2004, 116, 5812;
9. Angew. Chem., Int. Ed. 2004, 43, 5694.
10. Lyaskovskyy, V.; Fröhlich, R.; Würthwein, E.-U. Chem. Eur. J. In press. DOI: 10.1002/chem.200601491.
11. See, for example: Krause, N.; Hoffman-Röder, A. In Modern Organocupper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 145-166.
12. Fleming, I.; de Marigorta, E. M. J. Chem. Soc., Perkin Trans. 1 1999, 889.
13. Piers, E.; Boehringer, E. M.; Yee, J. G. K. J. Org. Chem. 1998, 63, 8642.
14. 2O. The precipitate was filtered off, and the filtrate was extracted with diethyl ether (3 x 30 mL). The combined organic layers were washed with 2 N sodium hydroxide solution and then with brine and were dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by flash chromatography, giving the respective compounds 11.
15. (a) Klötgen, S.; Würthwein, E.-U. Tetrahedron Lett. 1995, 36, 7085.
16. (b) Klötgen, S.; Fröhlich, R.; Würthwein, E.-U. Tetrahedron 1996, 52, 14801.
17. (c) Gerdes, K.; Sagar, P.; Fröhlich, R.; Wibbeling, B.; Würthwein, E.-U. Eur. J. Org. Chem. 2004, 3465.
18. See examples in: Lipshutz, B. H. In Organomethallics in Synthesis. A Manual, 2nd ed.; Schlosser, M., Ed.; Wiley: Chichester, 2004; pp 674-685.
19. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.