Organocatalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides

Angewandte Chemie - International Edition

Volumn 45, Issue 30, 2006, Pages 4966-4970

  Bartoli, Giuseppe ^a   Bosco, Marcella ^a   Carlone, Armando ^a   Cavalli, Andrea ^a   Locatelli, Manuela ^a   Mazzanti, Andrea ^a   Ricci, Paolo ^a   Sambri, Letizia ^a   Melchiorre, Paolo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Asymmetric catalysis; Cinchona alkaloids; Conjugate addition; Maleimides; Organocatalysis

Indexed keywords

CATALYSTS; CHEMICAL BONDS; ORGANIC POLYMERS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ASYMMETRIC CATALYSIS; CINCHONA ALKALOIDS; CONJUGATE ADDITION; MALEIMIDES; ORGANOCATALYSTS;

ORGANIC COMPOUNDS;

EID: 33746760189     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600370     Document Type: Article

References (56)

1. For reviews on the asymmetric construction of quaternary carbon centers, see: a) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363, and references therein;
2. b) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726;
3. Angew. Chem. Int. Ed. 2003, 42, 1688;
4. c) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402;
5. Angew. Chem. Int. Ed. 1998, 37, 388.
6. For some leading examples that rely on different strategies, see: a) F. Wu, H. Li, R. Hong, L. Deng, Angew. Chem. 2006, 118, 961;
7. Angew. Chem. Int. Ed. 2006, 45, 947;
8. b) B. K. Corkey, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 17 168;
9. c) P. Mauleòn, J. C. Carretero, Chem. Commun. 2005, 4961;
10. d) M. D. Augustin, L. Palais, A. Alexakis, Angew. Chem. 2005, 117, 1400;
11. Angew. Chem. Int. Ed. 2005, 44, 1376;
12. e) A. W. Hird, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 14 988.
13. For recent reviews on catalytic asymmetric conjugate additions, see: a) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829;
14. b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171.
15. For the catalytic asymmetric construction of adjacent tertiary and quaternary centers, see: a) T. B. Poulsen, C. Alemparte, S. Saaby, M. Bella, K. A. Jørgensen, Angew. Chem. 2005, 117, 2956;
16. Angew. Chem. Int. Ed. 2005, 44, 2896;
17. b) J. F. Austin, S.-G. Kim, C. J. Sinz, W.-J. Xiao, D. W. C. MacMillan, Proc. Natl. Acad. Sci. USA 2004, 101, 5482.
18. a) M. S. Taylor, D. N. Zalatan, A. M. Lerchner, E. N. Jacobsen, J. Am. Chem. Soc. 2005, 127, 1313;
19. b) Y. Hamashima, D. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11 240; see also reference [2a].
20. H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman, L. Deng, Angew. Chem. 2005, 117, 107;
21. Angew. Chem. Int. Ed. 2005, 44, 105.
22. M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 11 204.
23. For recent examples of the use of cinchona alkaloid derivatives as efficient chiral-base catalysts, see: a) S. Sobhani, D. Fielenbach, M. Marigo, T. C. Wabnitz, K. A. Jørgensen, Chem. Eur. J. 2005, 11, 5689;
24. b) G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, P. Melchiorre, L. Sambri, Angew. Chem. 2005, 117, 6375;
25. Angew. Chem. Int. Ed. 2005, 44, 6219;
26. for a recent review, see: c) S.-K. Tian, Y. Chen, J. Hang, L. Tang, P. McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621.
27. For general reviews on organocatalysis, see: a) Asymmetric Organocatalysis (Eds.: A. Berkessel, H. Gröger), Wiley-VCH, Weinheim, 2004;
28. b) Acc. Chem. Res. 2004, 37(8), special issue (Eds.: K. N. Houk, B. List);
29. c) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
30. Angew. Chem. Int. Ed. 2004, 43, 5138.
31. For some biological studies on enantioenriched α-substituted succinimides, see: a) S. Ahmed, Drug Des. Discovery 1996, 14, 77;
32. b) M. L. Curtin, R. B. Garland, H. R. Heyman, R. R. Frey, M. R. Michaelides, J. Li, L. J. Pease, K. B. Glaser, P. A. Marcotte, S. K. Davidsen, Bioorg. Med. Chem. Lett. 2002, 12, 2919 ;
33. for the synthetic derivatization of this useful scaffold to afford functionalized open-chain derivatives and substituted pyrrolidines, see: c) A. R. Katritzky, J. Yao, M. Qi, Y. Chou, D. J. Sikora, S. Davis, Heterocycles 1998, 48, 2677;
34. d) R. Ballini, G. Bosica, G. Cioci, D. Fiorini, M. Petrini, Tetrahedron 2003, 59, 3603.
35. a) R. Shintani, W.-L. Duan, T. Nagano, A. Okada, T. Hayashi, Angew. Chem. 2005, 117, 4687;
36. Angew. Chem. Int. Ed. 2005, 44, 4611;
37. b) R. Shintani, K. Ueyama, I. Yamada, T. Hayashi, Org. Lett. 2004, 6, 3425.
38. After our manuscript had been submitted, the use of the same strategy for asymmetric addition to substituted maleimides to afford quaternary stereocenters was reported: c) R. Shintani, W.-L. Duan, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 5628.
39. For selected examples, see: a) B. Vakulya, Sz. Varga, A. Csámpai, T. Soos, Org. Lett. 2005, 7, 1967;
40. b) S. H. McCooey, S. J. Connon, Angew. Chem. 2005, 117, 6525;
41. Angew. Chem. Int. Ed. 2005, 44, 6367;
42. c) Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc. 2006, 128, 3928.
43. a) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10 219;
44. b) S. Kawahara, A. Nakano, T. Esumi, Y. Iwabuchi, S. Hatakeyama, Org. Lett. 2003, 5, 3103.
45. a) H. Hiemstra, H. Wynberg, J. Am. Chem. Soc. 1981, 103, 417;
46. b) H. Wynberg, Top. Stereochem. 1986, 16, 87.
47. For quinine-catalyzed conjugate additions of carbon-centered nucleophiles with low selectivity, see: a) H. Wynberg, R. Helder, Tetrahedron Lett. 1975, 16, 4057;
48. b) G. Szöllösi, M. Bartók, Chirality 2001, 13, 614;
49. for a review, see: c) K. Kacprzak, J. Gawroñsky, Synthesis 2001, 961;
50. during our studies, two highly selective reactions catalyzed by natural cinchona alkaloids were reported: d) B. Török, M. Abid, G. London, J. Esquibel, M. Török, S. C. Mhadgut, P. Yan, G. K. S. Prakash, Angew. Chem. 2005, 117, 3146;
51. Angew. Chem. Int. Ed. 2005, 44, 3086;
52. e) S. Lou, B. M. Taoka, A. Ting, S. E. Schaus, J. Am. Chem. Soc. 2005, 127, 11 256.
53. For similar effects of the size of the ester group on the selectivity of organocatalytic asymmetric transformations, see references [2a] and [8a].
54. M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 5672; see also reference [6].
55. 2O to give fine colorless needles of a single diastereomer with the configuration shown in Equation (2). The same crystal used for X-ray crystallography was analyzed by chiral HPLC, which confirmed the presence of the major enantiomer. CCDC-296418 (5) and -605040 (4d) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
56. The relative configuration of 6 was assigned by using NMR spectroscopic analysis with extensive NOE interaction studies; see the Supporting Information for details.