Chiral bifunctional squaramide-catalyzed highly enantioselective michael addition of allomaltol to β,γ-unsaturated α-ketoesters

ChemCatChem

Volumn 6, Issue 8, 2014, Pages 2298-2304

  Liu, Yunting ^a   Wang, Qiaohui ^a   Wang, Youming ^a   Song, Haibin ^a   Zhou, Zhenghong ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

C C coupling; homogeneous catalysis; Michael addition; organocatalysis; small ring systems

Indexed keywords

ADDITION REACTIONS; CATALYSIS; REACTION KINETICS; SCAFFOLDS;

C-C COUPLING; HOMOGENEOUS CATALYSIS; MICHAEL ADDITIONS; ORGANOCATALYSIS; SMALL RING SYSTEMS;

ENANTIOSELECTIVITY;

EID: 84907466240     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201402168     Document Type: Article

References (48)

1. M. C. Pirrung, L. Deng, B. Lin, N. J. G. Webster, ChemBioChem 2008, 9, 360.
2. M. Raje, N. Hin, B. Duvall, D. V. Ferraris, J. F. Berry, A. G. Thomas, J. Alt, C. Rojas, B. S. Slusher, T. Tsukamoto, Bioorg. Med. Chem. Lett. 2013, 23, 3910
3. J. S. Chen, C.-i. Wei, R. S. Rolle, W. S. Otwell, M. O. Balaban, M. R. Marshall, J. Agric. Food Chem. 1991, 39, 1396.
4. S.-Y. Kwak, J.-M. Noh, S.-H. Park, J.-W. Byun, H.-R. Choi, K.-C. Park, Y.-S. Lee, Bioorg. Med. Chem. Lett. 2010, 20, 738
5. H. S. Rho, S. M. Ahn, D. S. Yoo, M. K. Kim, D. H. Cho, J. Y. Cho, Bioorg. Med. Chem. Lett. 2010, 20, 6569.
6. M. D. Aytemir, Ü. Çaliş, M. Özalp, Arch. Pharm. Pharm. Med. Chem. 2004, 337, 281
7. M. D. Aytemir, Ü. Çaliş, Arch. Pharm. Chem. Life Sci. 2010, 343, 173.
8. M. Yamato, K. Hashigaki, J. Sakai, Y. Kawasaki, S. Tsukagoshi, T. Tashiro, J. Med. Chem. 1987, 30, 117.
9. M. D. Aytemir, B. Özçelik, G. Karakaya, Bioorg. Med. Chem. Lett. 2013, 23, 3646.
10. M. D. Aytemir, B. Özçelik, Eur. J. Med. Chem. 2010, 45, 4089.
11. J. G. Atkinson, Y. Girard, J. Rokach, C. S. Rooney, C. S. McFarlane, A. Rackham, N. N. Share, J. Med. Chem. 1979, 22, 99.
12. P. A. Wender, N. D'Angelo, V. I. Elitzin, M. Ernst, E. E. Jackson-Ugueto, J. A. Kowalski, S. McKendry, M. Rehfeuter, R. Sun, Org. Lett. 2007, 9, 1829
13. P. A. Wender, J. L. Mascarenas, Tetrahedron Lett. 1992, 33, 2115
14. P. A. Wender, J. L. Mascarenas, J. Org. Chem. 1991, 56, 6267
15. P. A. Wender, F. E. McDonald, J. Am. Chem. Soc. 1990, 112, 4956.
16. J. Wang, Q. Zhang, H. Zhang, Y. Feng, W. Yuan, X. Zhang, Org. Biomol. Chem. 2012, 10, 2950
17. J. Kaeobamrung, J. Mahatthananchai, P. G. Zheng, J. W. Bode, J. Am. Chem. Soc. 2010, 132, 8810
18. J. Mahatthananchai, P. G. Zheng, J. W. Bode, Angew. Chem. Int. Ed. 2011, 50, 1673
19. Angew. Chem. 2011, 123, 1711
20. J. Mahatthananchai, J. Kaeobamrung, J. W. Bode, ACS Catal. 2012, 2, 494.
21. For recent reviews on organocatalytic conjugate additions, see: a) R. Somanathan, D. Chavez, F. A. Servin, J. A. Romero, A. Navarrete, M. Parra-Hake, G. Aguirre, C. Anaya de Parrodi, J. Gonzalez, Curr. Org. Chem. 2012, 16, 2440
22. P. Chauhan, S. S. Chimni, RSC Adv. 2012, 2, 6117
23. D. Enders, C. Wang, J. X. Liebich, Chem. Eur. J. 2009, 15, 11058
24. S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701
25. D. Almaşi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 299.
26. L. Wu, Y. Wang, H. Song, L. Tang, Z. Zhou, C. Tang, ChemCatChem 2014, 6, 649
27. K. Hu, Y. Wang, Z. Zhou, C. Tang, Tetrahedron 2014, 70, 181
28. Y. Liu, Y. Wang, H. Song, Z. Zhou, C. Tang, Adv. Synth. Catal. 2013, 355, 2544
29. H. Yu, Q. Wang, Y. Wang, H. Song, Z. Zhou, C. Tang, Chem. Asian J. 2013, 8, 2859
30. L. Wu, Y. Wang, H. Song, L. Tang, Z. Zhou, C. Tang, Chem. Asian J. 2013, 8, 2204
31. L. Wu, Y. Wang, H. Song, L. Tang, Z. Zhou, C. Tang, Adv. Synth. Catal. 2013, 355, 1053
32. A. Lu, K. Hu, Y. Wang, H. Song, Z. Zhou, J. Fang, C. Tang, J. Org. Chem. 2012, 77, 6208
33. R. Wu, X. Chang, A. Lu, Y. Wang, G. Wu, H. Song, Z. Zhou, C. Tang, Chem. Commun. 2011, 47, 5034
34. T. Liu, Y. Wang, G. Wu, H. Song, Z. Zhou, C. Tang, J. Org. Chem. 2011, 76, 4119
35. A. Lu, T. Liu, R. Wu, Y. Wang, G. Wu, Z. Zhou, J. Fang, C. Tang, J. Org. Chem. 2011, 76, 3872.
36. For reviews on thiourea-based organocatalysis, see: a) W.-Y. Siau, J. Wang, Catal. Sci. Technol. 2011, 1, 1298
37. B.; Han, J.-L. Li, Y.-C. Xiao, S.-L. Zhou, Y.-C. Chen, Curr. Org. Chem. 2011, 15, 4128
38. Y. Takemoto, Chem. Pharm. Bull. 2010, 58, 593
39. S. J. Connon, Chem. Eur. J. 2006, 12, 5418.
40. For a review on squaramide-based organocatalysis, see:, J. Alemán, A. Parra, H. Jiang, K. A. Jørgensen, Chem. Eur. J. 2011, 17, 6890.
41. Y.-F. Wang, K. Wang, W. Zhang, B.-B. Zhang, C.-X. Zhang, D.-Q. Xu, Eur. J. Org. Chem. 2012, 3691
42. Z. Dong, J. Feng, X. Fu, X. Liu, L. Lin, X. Feng, Chem. Eur. J. 2011, 17, 1118
43. Z. Dong, J. Feng, W. Cao, X. Liu, L. Lin, X. Feng, Tetrahedron Lett. 2011, 52, 3433
44. Y. Gao, Q. Ren, L. Wang, J. Wang, Chem. Eur. J. 2010, 16, 13068
45. X.-K. Chen, C.-W. Zheng, S.-L. Zhao, Z. Chai, Y.-Q. Yang, G. Zhao, W.-G. Cao, Adv. Synth. Catal. 2010, 352, 1648
46. M. A. Calter, J. Wang, Org. Lett. 2009, 11, 2205.
47. H. Wang, Y. Wang, H. Song, Z. Zhou, C. Tang, Eur. J. Org. Chem. 2013, 4844
48. K. Hu, A. Lu, Y. Wang, Z. Zhou, C. Tang, Tetrahedron: Asymmetry 2013, 24, 953.