Enantioselective diels-alder reactions with anomalous endo/exo selectivities using conformationally flexible chiral supramolecular catalysts

Angewandte Chemie - International Edition

Volumn 50, Issue 51, 2011, Pages 12189-12192

  Hatano, Manabu ^a   Mizuno, Tomokazu ^a   Izumiseki, Atsuto ^a   Usami, Ryota ^a   Asai, Takafumi ^a   Akakura, Matsujiro ^c   Ishihara, Kazuaki ^a,b  

^a NAGOYA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c AICHI UNIVERSITY OF EDUCATION   (Japan)

Author keywords

acroleins; asymmetric catalysis; cycloaddition; cyclopentadiene; supramolecular catalysis

Indexed keywords

ACROLEINS; ARYLBORONIC ACIDS; ASYMMETRIC CATALYSIS; CHIRAL DIOLS; CYCLOPENTADIENES; DIELS-ALDER REACTION; DIENOPHILES; ENANTIOSELECTIVE DIELS-ALDER REACTIONS; HIGH ENANTIOSELECTIVITY; IN-SITU; SUPRAMOLECULAR CATALYSIS; SUPRAMOLECULAR CATALYSTS; TRIS(PENTAFLUOROPHENYL) BORANE;

ALDEHYDES; CATALYSIS; CATALYSTS; CYCLOADDITION; ENANTIOSELECTIVITY; HERBICIDES; OLEFINS;

SUPRAMOLECULAR CHEMISTRY;

EID: 83755184091     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201106497     Document Type: Article

References (55)

1. R. Hoffmann, R. B. Woodward, J. Am. Chem. Soc. 1965, 87, 4388
2. J. I. García, J. A. Mayoral, L. Salvatella, Acc. Chem. Res. 2000, 33, 658
3. C. S. Wannere, A. Paul, R. Herges, K. N. Houk, H. F. Schaefer III, P. von R. Schleyer, J. Comput. Chem. 2007, 28, 344.
4. H. B. Kagan, O. Riant, Chem. Rev. 1992, 92, 1007
5. E. J. Corey, Angew. Chem. 2002, 114, 1724
6. Angew. Chem. Int. Ed. 2002, 41, 1650
7. K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742
8. Angew. Chem. Int. Ed. 2002, 41, 1668
9. P. Merino, E. Marqués-Lõpez, T. Tejero, R. P. Herrera, Synthesis 2010, 1
10. H. Du, K. Ding, in Handbook of Cyclization Reactions (Ed.:, S. Ma,), Wiley-VCH, Weinheim, 2010, pp. 1-57
11. K. Ishihara, A. Sakakura, in Science of Synthesis Stereoselective Synthesis, Vol. 3 (Ed.:, P. A. Evans,), Thieme, Stuttgart, 2011, pp. 67-123.
12. K. Maruoka, H. Imoto, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 12115.
13. T. Kano, Y. Tanaka, K. Maruoka, Org. Lett. 2006, 8, 2687
14. T. Kano, Y. Tanaka, K. Maruoka, Chem. Asian J. 2007, 2, 1161.
15. M. P. Sibi, X. Nie, J. P. Shackleford, L. M. Stanley, F. Bouret, Synlett 2008, 2655.
16. Y. Hayashi, S. Samanta, H. Gotoh, H. Ishikawa, Angew. Chem. 2008, 120, 6736
17. Angew. Chem. Int. Ed. 2008, 47, 6634.
18. M. Yoshizawa, J. K. Klosterman, M. Fujita, Angew. Chem. 2009, 121, 3470
19. Angew. Chem. Int. Ed. 2009, 48, 3418
20. M. D. Pluth, R. G. Bergman, K. N. Raymond, Acc. Chem. Res. 2009, 42, 1650.
21. M. Yoshizawa, M. Tamura, M. Fujita, Science 2006, 312, 251
22. Y. Nishioka, T. Yamaguchi, M. Yoshizawa, M. Fujita, J. Am. Chem. Soc. 2007, 129, 7000
23. G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1
24. T. S. Koblenz, J. Wassenaar, J. N. H. Reek, Chem. Soc. Rev. 2008, 37, 247
25. T. Murase, S. Horiuchi, M. Fujita, J. Am. Chem. Soc. 2010, 132, 2866
26. S. Horiuchi, Y. Nishioka, T. Murase, M. Fujita, Chem. Commun. 2010, 46, 3460
27. S. Horiuchi, T. Murase, M. Fujita, Chem. Asian J. 2011, 6, 1839.
28. M. Hatano, T. Miyamoto, K. Ishihara, Adv. Synth. Catal. 2005, 347, 1561
29. M. Hatano, T. Miyamoto, K. Ishihara, Synlett 2006, 1762
30. M. Hatano, T. Miyamoto, K. Ishihara, J. Org. Chem. 2006, 71, 6474
31. M. Hatano, K. Ishihara, Chem. Rec. 2008, 8, 143.
32. We used 4 Ã molecular sieves according to the reported procedure, as they might promote the complexation of boron BINOLates and remove coordinated water from the complexes., K. Ishihara, H. Kurihara, M. Matsumoto, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 6920.
33. M. A. Beckett, D. S. Brassington, M. E. Light, M. B. Hursthouse, J. Chem. Soc. Dalton Trans. 2001, 1768.
34. K. Ishihara, J. Kobayashi, K. Inanaga, H. Yamamoto, Synlett 2001, 394
35. K. Futatsugi, H. Yamamoto, Angew. Chem. 2005, 117, 1508
36. Angew. Chem. Int. Ed. 2005, 44, 1484.
37. Low catalytic activities of 5-a, (5-a + 6-a), and (5-a + 7) are reasonable. The BrÃnsted acidity of 5-a is not sufficient to catalyze the reaction. For the (5-a + 7) catalyst, the phosphoryl moieties of 5-a coordinate to 7, and thus the Lewis acidity of 7 is decreased. For the (5-a + 6-a) catalyst, the corresponding boron BINOLate is not reactive because it lacks the conjugated activation by Lewis acid 7. Therefore, the catalytic activity of the conjugates based on 5-a decreased if either 6-a or 7 were not present.
38. E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966.
39. E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979
40. K. T. Sprott, E. J. Corey, Org. Lett. 2003, 5, 2465.
41. For the exo-selective Diels-Alder reaction of 2-c, see
42. E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931
43. Angew. Chem. Int. Ed. Engl. 1994, 33, 1856
44. Y. Yamashita, T. Katsuki, Synlett 1995, 829
45. T.-P. Loh, R.-B. Wang, K.-Y. Sim, Tetrahedron Lett. 1996, 37, 2989
46. Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502
47. W. A. J. Starmans, R. W. A. Walgers, L. Thijs, R. de Gelder, J. M. M. Smits, B. Zwanenburg, Tetrahedron 1998, 54, 4991
48. D. A. Evans, D. M. Barnes, J. S. Johnson, T. Lectka, P. von Matt, S. J. Miller, J. A. Murry, R. D. Norcross, E. A. Shaughnessy, K. R. Campos, J. Am. Chem. Soc. 1999, 121, 7582
49. J. W. Faller, B. J. Grimmond, D. G. D'Alliessi, J. Am. Chem. Soc. 2001, 123, 2525
50. A. J. Davenport, D. L. Davies, J. Fawcett, D. R. Russell, J. Chem. Soc. Perkin Trans. 1 2001, 1500
51. E. J. Corey, T. Shibata, T. W. Lee, J. Am. Chem. Soc. 2002, 124, 3808
52. Y.-C. Teo, T.-P. Loh, Org. Lett. 2005, 7, 2539
53. T. Kano, T. Konishi, S. Konishi, K. Maruoka, Tetrahedron Lett. 2006, 47, 873
54. F. Fu, Y.-C. Teo, T.-P. Loh, Org. Lett. 2006, 8, 5999.
55. -1. See the Supporting Information for the detailed results.