Catalytic, enantioselective bifunctional inverse electron demand Hetero-Diels-Alder reactions of ketene enolates and o-benzoquinone diimides

Journal of the American Chemical Society

Volumn 128, Issue 41, 2006, Pages 13370-13371

  Abraham, Ciby J ^a   Paull, Daniel H ^a   Scerba, Michael T ^a   Grebinski, James W ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; IMIDE; KETENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; DIELS ALDER REACTION; ELECTRON TRANSPORT; ENANTIOSELECTIVITY; INFRARED SPECTROSCOPY; REACTION ANALYSIS; ROOM TEMPERATURE; SYNTHESIS;

ALCOHOLS; ALKADIENES; BENZOQUINONES; CATALYSIS; ELECTRONS; ETHYLENES; IMIDES; KETONES; MODELS, CHEMICAL; STEREOISOMERISM;

EID: 33750071714     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065754d     Document Type: Article

References (24)

1. (a) For review, see Carmona, D.; Pilar Lamata, M.; Oro, L. A. Coord. Chem. Rev. 2000, 200-202, 717-772.
2. (b) For a recent example, see Unni, A. K.; Takenaka, N.; Yamamoto, H.; Rawal, V. H. J. Am. Chem. Soc. 2005, 127, 1336-1337.
3. For review, see List, B. Chem. Commun. 2006, 8, 819-824.
4. (a) Marko, I. E.; Evans, G. R.; Seres, P.; Chelle, I.; Janousek, Z. Pure Appl. Chem. 1996, 68, 113-122.
5. (b) Boger, D. L.; Patel, M. Prog. Heterocycl. Chem. 1989, 1, 30-64.
6. (a) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 6626-6635.
7. (b) Bekele, T.; Shah, M. H.; Wolfer, J.; Abraham, C. J.; Weatherwax, A.; Lectka, T. J. Am. Chem. Soc. 2006, 128, 1810-1811.
8. (a) DiMauro, E. F.; Marnai, A.; Kozlowski, M. C. Organometallics 2003, 22, 850-855.
9. (b) France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. J. Am. Chem. Soc. 2005, 127, 1206-1215.
10. (c) Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 10, 1491-1508.
11. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893-930 and references therein.
12. Gupta, D.; Ghosh, N. N.; Chandra, R. Bioorg. Med. Chem. Lett. 2005. 15, 1019-1022.
13. Rösner, M.; Billhardt-Troughton, U.-M.; Kirsh, R.; Kleim, J.-P.; Meichsner, C.; Riess, G.; Winkler, I. U.S. Patent 5,723, 461, 1998.
14. a) Sarges, R.; Lyga, J. W. J. Heterocycl. Chem. 1988, 25, 1475-1479.
15. (b) Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997-10998.
16. Lee, L.; Murray, W. V.; Rivero, R. A. J. Org. Chem. 1997, 62, 3874-3879 and references therein.
17. Morales, G. A.; Corbett, J. W.; DeGrado, W. F. J. Org. Chem. 1998, 63, 1172-1177.
18. Jones, Z.; Groneberg, R.; Drew, M.; Eary, C. T. U.S. Patent 20050282812, 2005.
19. (a) Lee, J.; Murray, W. V.; Rivero, R. A. J. Org. Chem. 1997, 62, 3874-3879.
20. (b) Zaragoza, F.; Stephensen, H. J. Org. Chem. 1999, 64, 2555-2557.
21. Adams, R.; Way, J. W. J. Am. Chem. Soc. 1954, 76, 2763-2769.
22. For review, see Nair, V.; Dhanya, R.; Rajesh, C.; Devipriya, S. Synlett 2005, 16, 2407-2419.
23. The experimental values are consistent with PM3 vibrational analyses performed by the Spartan program (version 5.0.3).
24. Ikeda, M.; Ohno, K.; Uno, T.; Tamura, Y. Tetrahedron Lett. 1980, 21, 3403-3406.