Complete characterization of a chiral lewis acid - Product complex for the enantioselective diels - Alder reaction between methacrolein and cyclopentadiene: mechanistic considerations

Organometallics

Volumn 26, Issue 25, 2007, Pages 6493-6496

  Carmona, Daniel ^a   Lamata, M Pilar ^a   Viguri, Fernando ^a   Rodríguez, Ricardo ^a   Barba, Carmen ^a   Lahoz, Fernando J ^a   Martín, M Luisa ^a   Oro, Luis A ^a   Salvatella, Luis ^a  

^a CSIC UZA Instituto de Sintesis Quimica y Catalisis Homogenea ISQCH   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHARACTERIZATION; REACTION KINETICS; X RAY CRYSTALLOGRAPHY;

CYCLOPENTADIENE; DIENOPHILE; METHACROLEIN;

ENANTIOSELECTIVITY;

EID: 37249009168     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700717e     Document Type: Article

References (22)

1. Fringuelli, F.; Taticchi, A. In The Diels-Alder Reaction. Selected Practical Methods; Wiley: New York, 2002.
2. (a) Hashimoto, S.-I.; Komeshima, N.; Koga, K. J. Chem. Soc., Chem. Commun. 1979, 437.
3. (b) Takemura, H.; Komeshima, N.; Takahashi, I.; Hashimoto, S.-I.; Ikota, N.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1987, 28, 5687.
4. For example, see: (a) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis, Vol. III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Chapter 33.1, p 1177.
5. (b) Carmona, D.; Lamata, M. P.; Oro, L. A. Coord. Chem. Rev. 2000, 200-202, 717.
6. (c) Hayashi, Y. In Cycloaddition Reactions In Organic Synthesis; Kobayashi, S., Jørgensen, K. A., Eds.; Wiley-VCH; Weinheim, 2002; Chapter 1, p 5.
7. (a) Corey, E. J.; Loh, T.-P.; Roper, T. D.; Azimioara, M. D.; Noe, M. C. J. Am. Chem. Soc. 1992, 114, 8290-8292.
8. (b) Corey, E. J.; Loh, T.-P.; Sarshar, S.; Azimioara, M. Tetrahedron Lett. 1992, 33, 6945.
9. (c) Ishihara, K.; Gao, Q.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10412-10413.
10. (d) Carmona, D.; Cativiela, C.; Elipe, S.; Lahoz, F. J.; Lamata, M. P.; López-Ram de Viu, M. P.; Oro, L. A.; Vega, C.; Viguri, F. Chem. Commun. 1997, 2351.
11. (e) Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1219.
12. (f) Davenport, A. J.; Davies, D. L.; Fawcett, J.; Garratt, S. A.; Russell, D. R. J. Chem. Soc, Dalton Trans. 2000, 4432.
13. (g) Carmona, D.; Lamata, M. P.; Viguri, F.; Rodriguez, R.; Oro, L. A.; Balana, A. I.; Lahoz, F. J.; Tejero, T.; Merino, P.; Franco, S.; Montesa, I. J. Am. Chem. Soc. 2004, 126, 2716.
14. (h) Carmona, D.; Lamata, M. P.; Viguri, F.; Rodríguez, R.; Oro, L. A.; Lahoz; Balana, A. I.; Tejero, T.; Merino, P. J. Am. Chem. Soc. 2005, 127, 13386.
15. Barba, C.; Carmona, D.; García, J. I.; Lamata, M. P.; Mayoral, J. A.; Salvatella, L.; Viguri, F. J. Org. Chem. 2006, 71, 9831 and references therein.
16. Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1993, 115, 3133.
17. Stanley, K.; Baird, M. C. J. Am. Chem. Soc. 1975, 97, 6598.
18. (a) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, T. J. Am. Chem. Soc. 1999, 121, 7559.
19. (b) Odenkirk, W.; Rheingold, A. L.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 6392.
20. Furuta, K.; Shimizu, S.; Miwa, Y.; Yamamoto, H. J. Org. Chem. 1989, 54, 1481.
21. SHELXTL+ Package v 6.10; Bruker AXS: Madison, WI, 2000.
22. Sheldrick, G. M. SHELXS-86 and SHELXL-91; University of Göttingen: Göttingen, Germany, 1997.