On the mechanism of cyclization of 5-hexenylchromate intermediates in the reactions of fischer carbene complexes with a lithium enolate and allylmagnesium bromide

Journal of Organic Chemistry

Volumn 74, Issue 18, 2009, Pages 7059-7066

  Campomanes, Pablo ^a,b   Flórez, Josefa ^a   Pérez Sánchez, Iván ^a   Suero, Marcos G ^a   Sordo, Tomás L ^a   Menéndez, M Isabel ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE MOLECULES; CARBENE COMPLEXES; CATALYTIC ROLE; CHEMICAL EQUATIONS; FISCHER CARBENE COMPLEX; H MIGRATION; LITHIUM ENOLATES; PCM MODEL; PENTACARBONYL; POLARIZABLE CONTINUUM MODEL; REACTION MEDIUM; TRANSITION STATE;

AMINES; CHEMICAL REACTIONS; CHROMIUM; CONTINUUM MECHANICS; DENSITY FUNCTIONAL THEORY; KETONES; LITHIUM; ORGANIC SOLVENTS; STEREOCHEMISTRY;

CHROMIUM COMPOUNDS;

ALKYL GROUP; ALLYL COMPOUND; AMINE; BROMIDE; CARBENOID; CARBONYL DERIVATIVE; CHROMIC ACID; KETONE DERIVATIVE; LITHIUM DERIVATIVE; MAGNESIUM DERIVATIVE; METHYL GROUP;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; CYCLIZATION; DENSITY FUNCTIONAL THEORY; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 70249115768     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901353s     Document Type: Article

References (25)

1. Multicomponent Reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
2. Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471-1499.
3. Mihovilovic, M. D.; Stanetty, P. Angew. Chem., Int. Ed. 2007, 46, 3612-3615.
4. Metal Carbenes in Organic Synthesis; Topics in Organometallic Chemistry, Vol.13; Dötz, K. H., Ed.; Springer-Verlag: Berlin, Germany, 2004.
5. Barluenga, J.; Fernández-Rodríguez, M. A.; Aguilar, E. J. Organomet. Chem. 2005, 690, 539-587.
6. Barluenga, J.; Pérez-Sánchez, I.; Rubio, E.; Flórez, J. Angew. Chem., Int. Ed. 2003, 42, 5860-5863.
7. Barluenga, J.; Pérez-Sánchez, I.; Suero, M. G.; Rubio, E.; Flórez, J. Chem.; Eur. J. 2006, 12, 7225-7235.
8. Increasing alkyl substitution on an open chain is known to facilitate the cyclization processes: (a) Sammes, P. G.; Weller, D. J. Synthesis 1995, 1205-1222.
9. (b) Pawlowski, M.; Maurin, J. K.; Leniewski, A.; Wojtasiewicz, K.; Czarnocki, Z. Heterocycles 2005, 65, 9-22.
10. Becke, A. B. J. Chem. Phys. 1993, 98, 5648-5662.
11. Becke, A. B. Phys. Rev. A 1988, 38, 3098-3100.
12. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
13. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
14. 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 B.04; Gaussian, Inc., Wallingford, CT, 2004.
15. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161.
16. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 84, 5523-5527.
17. McQuarrie, D. A. Statistical Mechanics; Harper & Row: New York, 1986.
18. Rivail, J. L.; Rinaldi, D.; Ruiz-López, M. F. In Theoretical and Computational Model for Organic Chemistry; Formosinho, S. J., Csizmadia, I. G., Arnaut, L., Eds.; NATO ASI Series C; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1991.
19. Cramer, C. J.; Truhlar, D. G. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1995.
20. Rivail, J. L.; Rinaldi, D. In Computational Chemistry: Review of Current Trends; Leszczynski, J., Ed.; World Scientific: New York, 1995.
21. Cramer, C. J.; Truhlar, D. G. Chem. Rev. 1999, 99, 2161-2200.
22. Claverie, P. In Quantum Theory of Chemical Reactions; Daudel, R., Pullman, A., Salem, L., Veillard, A., Eds.; Reidel: Dordrecht, The Netherlands, 1982.
23. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094.
24. Tomasi, J.; Cammi, R. J. Comput. Chem. 1996, 16, 1449-1458.
25. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221.