Efficient direct asymmetric vinylogous Michael addition reactions of γ-butenolides to chalcones catalyzed by vicinal primary-diamine salts

Chemical Communications

Volumn 46, Issue 12, 2010, Pages 2124-2126

  Wang, Junfeng ^a   Qi, Chao ^a   Ge, Zemei ^a   Cheng, Tieming ^a   Li, Runtao ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BUTENOLIDE; CHALCONE DERIVATIVE; DIAMINE DERIVATIVE; DIAMINE SALT; DIIMINIUM; GAMMA BUTENOLIDE; IMINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; COMPLEX FORMATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; MICHAEL ADDITION; PHASE TRANSITION; STEREOCHEMISTRY;

EID: 77949388269     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b923925a     Document Type: Article

References (52)

1. For reviews encompassing major classes of butenolide-containing natural products, see: (a) Furanocembranoid diterpenes: A. D. Rodriguez, Tetrahedron, 1995, 51, 4571;
2. (b) Acetogenins: F. W. Alali, X.-X. Liu and J. L. McLaughlin, J. Nat. Prod., 1999, 62, 504;
3. (c) C. J. Smith, D. Abbanat, V. S. Bernan,W.M.Maiese, M. Greenstein, J. Jompa, A. Tahir and C. M. Ireland, J. Nat. Prod., 2000, 63, 142;
4. (d) Cardiac steroids or cardenolides: J. R. Hanson, Nat. Prod. Rep., 2002, 19, 381;
5. (e) R.-T. Li, Q.-B. Han, Y.-T. Zheng, R.-R. Wang, L.-M. Yang, Y. Lu, S.-Q. Sang, Q.-T. Zheng, Q.-S. Zhao and H.-D. Sun, Chem. Commun., 2005, 2936;
6. (f) A. Dalpiaz, B. Pavan, M. Scaglianti, F. Vitali, F. Bortolotti, C. Biondi, A. Scatturin and S.Manfredini, Int. J. Pharm., 2005, 291, 171;
7. (g) S. Antane, C. E. Caueld,W. Hu, D. Keeney, P. Labthavikul, K. Morris, S. M. Naughton, P. J. Petersen, B. A. Rasmussen, G. Singh and Y. Yang, Bioorg. Med. Chem. Lett., 2006, 16, 176.
8. For examples, see: (a) Y. S. Rao, Chem. Rev., 1976, 76, 625;
9. (b) E. Fukusaki, S. Senda, Y. Nakazono and T. Omata, Tetrahedron, 1991, 47, 6223;
10. (c) K. Mori, Tetrahedron, 1989, 45, 3233;
11. (d) J. W. Wheeler, G. M. Happ, J. Araujo and J. M. Pasteels, Tetrahedron Lett., 1972, 13, 4635;
12. (e) R. Bloch and L. Gilbert, J. Org. Chem., 1987, 52, 4603;
13. (f) L. Thijs, W. P. Waanders, E. H. M. Stokkingreef and B. Zwanenburg, Recl. Trav. Chim. Pays-Bas., 1986, 105, 332.
14. (a) G. Casiraghi and G. Rassu, Synthesis, 1995, 607;
15. (b) G. Casiraghi, G. Rassu, F. Zanardi and L. Battistini, in Advances in Asymmetric Synthesis, ed. A. Haassner, JAI Press, Stamford, 1998, vol. 3, pp. 113-189;
16. (c) G. Rassu, F. Zanardi, L. Battistini and G. Casiraghi, Synlett, 1999, 1333.
17. (a) For a review on the vinylogous aldol reaction in butenolide synthesis, see: G. Casiraghi, F. Zanardi, G. Appendino and G. Rassu, Chem. Rev., 2000, 100, 1929;
18. (b) For a review on the vinylogous Michael reaction in butenolide synthesis, see: J. Christoffers, Synlett, 2001, 723.
19. For reviews on the vinylogous Mannich reaction in butenolide synthesis, see: (a) S. K. Bur and S. F. Martin, Tetrahedron, 2001, 57, 3221;
20. (b) S. F. Martin, Acc. Chem. Res., 2002, 35, 895.
21. (a) K. Narasaka and T. Mukaiyama, Chem. Lett., 1974, 1223;
22. (b) K. Narasaka, K. Soai, Y. Aikawa and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1976, 49, 779;
23. (c) K. Saigo, M. Osaki and T. Mukaiyama, Chem. Lett., 1976, 163;
24. (d) T. Fukuyama and L. Yang, Tetrahedron Lett., 1986, 27, 6299;
25. (e) T. Fukuyama and L. Yang, J. Am. Chem. Soc., 1987, 109, 7881;
26. (f) T. Fukuyama and L. Yang, J. Am. Chem. Soc., 1989, 111, 8303;
27. (g) A. M. Brimble, T. M. Brimble and J. J. Gibson, J. Chem. Soc., Perkin Trans. 1, 1989, 179;
28. (h) A. M. Brimble, J. L. Duncalf and C. W. D. Reid, Tetrahedron: Asymmetry, 1995, 6, 263;
29. (i) T. Okano, S. Eguchi and Y. Hayakawa, Tetrahedron, 2000, 56, 6219.
30. (a) G. Desimoni, P. Quadrelli and P. Righetti, Tetrahedron, 1990, 46, 2927;
31. (b) G. Desimoni, P. Quadrelli, G. Faita, G. Mellerio, P. Righetti and C. Zanelli, Gazz. Chim. Ital., 1992, 122, 269.
32. (a) C. Botteghi, S. Paganelli, A. Schionato, C. Boga and A. Fava, J. Mol. Catal., 1991, 66, 7;
33. (b) J. Christoffers, Liebigs Ann./Recl., 1997, 1353.
34. M. Sawamura, H. Hamashima and Y. Ito, Tetrahedron, 1994, 50, 4439.
35. S. Kobayashi, S. Suda, M. Yamada and T. Mukaiyama, Chem. Lett., 1994, 97.
36. (a) J. M. Betancort and C. F. Barbas III, Org. Lett., 2001, 3, 3737;
37. (b) N. Halland, R. G. Hazell and K. A. Jøgensen, J. Org. Chem., 2002, 67, 8331;
38. (c) N. Halland, P. S. Aburel and K. A. Jøgensen, Angew. Chem., Int. Ed., 2003, 42, 661;
39. (d) H. Li, Y. Wang, L. Tang and L. Deng, J. Am. Chem. Soc., 2004, 126, 9906;
40. (e) T. Okino, Y. Hoashi, T. Furukawa, X. Xu and Y. Takemoto, J. Am. Chem. Soc., 2005, 127, 119;
41. (f) J. Lu, F. Liu and T. P. Loh, Adv. Synth. Catal., 2008, 350, 1796;
42. (g) J. Lu, F. Liu and T. P. Loh, Adv. Synth. Catal., 2008, 350, 1781.
43. S. P. Brown, N. C. Goodwin and D. W. C. MacMillan, J. Am. Chem. Soc., 2003, 125, 1192.
44. B. M. Trost and J. Hitce, J. Am. Chem. Soc., 2009, 131, 4572.
45. (a) F. Beecham, Tetrahedron Lett., 1972, 13, 1669;
46. (b) W. Stocklin, T. G. Waddell and T. A. Geisman, Tetrahedron, 1970, 26, 2397;
47. (c) G. Snatzke, Angew. Chem., Int. Ed. Engl., 1968, 7, 14;
48. (d) G. Snatzke, Tetrahedron, 1965, 21, 413 and 439;
49. (e) L. G. Yao, H. L. Liu, Y. W. Guo and E. Mollo, Helv. Chim. Acta, 2009, 92, 1085.
50. (a) A. Gypser, C. Bulow and H. D. Scharf, Tetrahedron, 1995, 51, 1921;
51. (b) J. Bernstein, U. Shmeuli, E. Zadock, Y. Kashman and I. Néeman, Tetrahedron, 1974, 30, 2817.
52. H. Kim, C. Yen, P. Preston and J. Chin, Org. Lett., 2006, 8, 5239.