Synthesis of 3-substituted 1,5-aldehyde esters via an organocatalytic highly enantioselective conjugate addition of new carbonylmethyl 2-pyridinylsulfone to enals

Chemical Communications

Volumn 48, Issue 1, 2012, Pages 148-150

  Deng, Jing ^a   Wang, Fei ^b   Yan, Wenzhong ^a   Zhu, Jin ^a   Jiang, Hualiang ^a   Wang, Wei ^a,c   Li, Jian ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b Chinese Pharmacopoeia Commission   (China)

^c UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CARBONYLMETHYL 2 PYRIDINYLSULFONE; ESTER DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; ENANTIOSELECTIVITY;

EID: 82355163567     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c1cc15714k     Document Type: Article

References (48)

1. J. D. Connolly and R. A. Hill, Dictionary of Terpenoids, Chapman and Hall, London, 1991, vol. 1, p. 476.
2. M. Kidwai, P. Sapra, K. R. Bhuskan, Curr. Med. Chem. 1999, 6, 195.
3. K. Bush, M. Macielag, M. Weidner-Wells, Curr. Opin. Microbiol. 2004, 7, 466.
4. D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635.
5. D. A. Evans, J. S. Johnson, J. Am. Chem. Soc. 1998, 120, 4895.
6. D. Enders, B. E. M. Rendenbach, Chem. Ber. 1987, 120, 1223.
7. Catalytic asymmetric conjugate reactions, ed. A. Cordova, Wiley-VCH, Weinheim, Germany, 2010.
8. J. L. Vicario, E. Reyes, D. Dadia and L. Carrillo, in Catalytic asymmetric conjugate reactions, ed. A. Cordova, Wiley-VCH, Weinheim, Germany, 2010, ch. 6, p. 619.
9. S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. Int. Ed. 2006, 45, 4305.
10. F. Wu, R. Hong, J. Khan, X. Liu, L. Deng, Angew. Chem. Int. Ed. 2006, 45, 4301.
11. Y. Wang, P. Li, X. Liang, J. Ye, Adv. Synth. Catal. 2008, 350, 1383.
12. A. Ma, S. Zhu, D. Ma, Tetrahedron Lett. 2008, 49, 3075.
13. Y. Hayashi, M. Toyoshima, H. Gotoh, H. Ishikawa, Org. Lett. 2009, 11, 45.
14. A.-N. Alba, X. Companyo, A. Moyano, R. Rios, Chem.-Eur. J. 2009, 15, 7035.
15. I. Fleischer, P. A. Ivana, Chem.-Eur. J. 2010, 16, 95.
16. A. Carlone, M. Marigo, C. North, A. Landa, K. A. Jørgensen, Chem. Commun. 2006, 4928.
17. C. Zhong, Y. Chen, L. Petersen, N. G. Akhmedov, X. Shi, Angew. Chem. Int. Ed. 2009, 48, 1279.
18. S. K. Ghosh, Z. Zheng, B. Ni, Adv. Synth. Catal. 2010, 352, 2378.
19. M. Kamlar, N. Bravo, A.-N. R. Alba, S. Hybelbauerova, I. Cisarova, J. Vesely, A. Moyano, R. Rios, Eur. J. Org. Chem. 2010, 5464.
20. T. Furukawa, Y. Goto, J. Kawazoe, E. Tokunaga, S. Nakamura, Y. Yang, H. Du, A. Kakehi, M. Shiro, N. Shibata, Angew. Chem. Int. Ed. 2010, 49, 1642.
21. A.-N. Alba, X. Companyo, A. Moyano, R. Rios, Chem.-Eur. J. 2009, 15, 7035.
22. A.-N. Alba, X. Companyo, A. Moyano, R. Rios, Chem.-Eur. J. 2009, 15, 11095.
23. D. A. Alonso, S. Kitagaki, N. Utsumi, C. F. Barbas III, Angew. Chem. Int. Ed. 2008, 47, 4588.
24. J. Wang, H. Li, L.-S. Zu, W. Jiang, H.-X. Xie, W.-H. Duan, W. Wang, J. Am. Chem. Soc. 2006, 128, 12652.
25. L.-S. Zu, H.-X. Xie, H. Li, J. Wang, W. Wang, Adv. Synth. Catal. 2007, 349, 2660.
26. L. Zu, H. Xie, H. Li, J. Wang, X. Yu, W. Wang, Chem.-Eur. J. 2008, 14, 6333.
27. S.-L. Zhang, J. Li, S.-H. Zhao, W. Wang, Tetrahedron Lett. 2010, 51, 1766.
28. H. Li, Y.-F. Ji, J. Li, S.-L. Zhang, C.-G. Yu, W. Wang, Sci. China Chem. 2010, 53, 135.
29. S.-L. Zhang, Y.-N. Zhang, Y.-F. Ji, H. Li, W. Wang, Chem. Commun. 2009, 4886.
30. S.-L. Zhang, H.-X. Xie, J. Zhu, H. Li, X.-S. Zhang, J. Li, W. Wang, Nat. Commun. 2011, 2, 1214.
31. A.-N. R. Alba, X. Companyo, R. Rios, Chem. Soc. Rev. 2010, 39, 2018.
32. M. Nielsen, C. B. Jacobsen, K. A. Jørgensen, Angew. Chem. Int. Ed. 2010, 49, 2668.
33. A. El-Awa, M. N. Noshi, X. M. Jourdin, P. L. Fuchs, Chem. Rev. 2009, 109, 2315.
34. L. Jiang, Q. Lei, X. Huang, H.-L. Cui, X. Zhou, Y.-C. Chen, Chem.-Eur. J. 2011, 17, 9489.
35. M. G. Brant, C. M. Bromba, J. E. Wulff, J. Org. Chem. 2010, 75, 6312.
36. N. Holub, H. Jiang, M. W. Paixão, C. Tiberi, K. A. Jørgensen, Chem.-Eur. J. 2010, 16, 4337.
37. J. L. García Ruano, V. Marcos, J. Alemán, Chem. Commun. 2009, 4435.
38. M. Nielsen, C. B. Jacobsen, M. W. Paixão, N. Holub, K. A. Jørgensen, J. Am. Chem. Soc. 2009, 131, 10581.
39. H. Li, J. Song, X. Liu, L. Deng, J. Am. Chem. Soc. 2005, 127, 8948.
40. A. Quintard, A. Alexakis, Chem.-Eur. J. 2009, 15, 11109.
41. Q. Zhu, Y. Lu, Org. Lett. 2009, 11, 1721.
42. A. Landa, M. Maestro, C. Masdeu, A. Puente, S. Vera, M. Oiarbide, C. Palomo, Chem.-Eur. J. 2009, 15, 1562.
43. A.-N. Alba, X. Companyo, G. Valero, A. Moyano, R. Rios, Chem.-Eur. J. 2010, 16, 5354.
44. E. Rodrigo, S. Morales, S. Duce, J. L. G. Ruano, M. B. Cid, Chem. Commun. 2011, 47, 11267.
45. J. B. Baudin, G. Hareau, S. A. Julia, Tetrahedron Lett. 1991, 32, 1175.
46. A. Mielgo, C. Palomo, Chem.-Asian J. 2008, 3, 922.
47. N. A. Magomedov, P. L. Ruggiero, Y.-C. Tang, Org. Lett. 2004, 6, 3373.
48. J.-M. Zhang, E. A. Polishchuk, J. Chen, M. A. Ciufolini, J. Org. Chem. 2009, 74, 9140.