Chiral 1,1′-binaphthyl-2,2′-diammonium salt catalysts for the enantioselective Diels-Alder reaction with α-acyloxyacroleins

Organic Letters

Volumn 8, Issue 11, 2006, Pages 2229-2232

  Sakakura, Akira ^a   Suzuki, Kenji ^a   Nakano, Kazuhiko ^a   Ishihara, Kazuaki ^a  

^a NAGOYA UNIVERSITY   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 33745725832     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060490l     Document Type: Article

References (35)

1. For review, see: Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650.
2. (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
3. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458.
4. For chiral organocatalysts for Diels-Alder reactions, see: (a) Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature 2003, 424, 146.
5. (b) Kim, K. H.; Lee, K. S.; Lee, D.-W.; Ko, D.-H.; Ha, D.-C. Tetrahedron Lett. 2005, 46, 5991.
6. (c) Lemay, M.; Ogilvie, W. W. Org. Lett. 2005, 7, 4141.
7. For a recent review on hydrogen-bonding catalysis, see: Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520.
8. MacMillan failed to activate methacrolein with a secondary ammonium salt: Kunz, R. K.; MacMillan D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
9. Ishihara, K.; Nakano, K. J. Am. Chem. Soc. 2005, 127, 10504.
10. (a) Corey, E. J.; Loh, T.-P. J. Am. Chem. Soc. 1991, 113, 8966.
11. (b) Marshall, J. A.; Xie, S. J. Org. Chem. 1992, 57, 2987.
12. (c) Corey, E. J.; Cywin, C. L. J. Org. Chem. 1992, 57, 7372.
13. (d) Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979.
14. (e) Ishihara, K.; Qingzhi, G.; Yamamoto, H. J. Org. Chem. 1993, 58, 6917.
15. (f) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561.
16. (g) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611.
17. (h) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049.
18. (i) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920.
19. (j) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808.
20. Funk, R. L.; Yost, K. J., III. J. Org. Chem. 1996, 61, 2598.
21. 3H is a weaker Brønsted acid than TsOH. (a) Ishihara, K.; Nakagawa, S.; Sakakura, A. J. Am. Chem. Soc. 2005, 127, 4168.
22. (b) Sakakura, A.; Nakagawa, S.; Ishihara, K. Tetrahedron 2006, 62, 422.
23. (a) Greene, A. E.; Le Drian, C.; Crabbé, P. J. Am. Chem. Soc. 1980, 102, 7583.
24. (b) Salomon, R. G.; Sachinvala, N. D.; Roy, S.; Basu, B.; Raychaudhuri, S. R.; Miller, D. B.; Sharma, R. B. J. Am. Chem. Soc. 1991, 113, 3085.
25. (c) Marschner, C.; Baumgartner, J.; Griemgl, H. J. Org. Chem. 1995, 60, 5224.
26. (d) Wang, G. T.; Wang, S.; Chen, Y.; Gentles, R.; Sowin, T. J. Org. Chem. 2001, 66, 2052.
27. (e) Zhu, X.-F.; Nydegger, F.; Gossauer, A. Helv. Chim. Acta 2004, 87, 2245.
28. The reaction conducted in the presence of water (100 mol %) gave similar results. When the reaction was carried out in the presence of more than 500 mol % of water, solvent was partially frozen and the reactivity was decreased.
29. 2, cyclopentadiene polymerized and the Diels-Alder adducts were obtained with low enantioselectivity.
30. (a) Evans, D. A.; Golob, A. M.; Mandel, N. S.; Mandel, G. S. J. Am. Chem. Soc. 1978, 100, 8170.
31. (b) Kozikowski, A. P.; Schemissing, R. J. J. Org. Chem. 1983, 48, 1000.
32. (c) Demuth, M.; Chandrasekhar, S.; Schaffner, K. J. Am. Chem. Soc. 1984, 106, 1092.
33. (d) Smith, A. B., III; Empfield, J. R.; Rivero, R. A.; Vaccaro, H. A.; Duan, J. J.-W.; Sulikowski, M. M. J. Am. Chem. Soc. 1992, 114, 9419.
34. (a) Thadani, A. N.; Stankovic, A. R.; Rawal, V. H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5846.
35. 2 = 0.1613, GOF = 1.063. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: int. code + 44-(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk]. Supplementary publication no. CCDC-286812.