Asymmetric Michael addition of arylthiols to α,β-unsaturated carbonyl compounds catalyzed by bifunctional organocatalysts

Synlett

Volumn , Issue 4, 2005, Pages 603-606

  Li, Bang Jing ^b   Jiang, Lin ^a   Liu, Min ^a   Chen, Ying Chun ^a   Ding, Li Sheng ^b   Wu, Yong ^a  

^a SICHUAN UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

Asymmetric Michael addition; Asymmetric protonation; Bifunctional organocatalyst; Hydrogen bonding; Thiourea

Indexed keywords

CARBONYL DERIVATIVE; THIOL DERIVATIVE; THIOUREA DERIVATIVE;

ARTICLE; CATALYST; ENANTIOSELECTIVITY; HYDROGEN BOND; MICHAEL ADDITION; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 15444366940     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-863710     Document Type: Article

References (50)

1. For recent reviews on organocatalysis involving hydrogen bonding, see: (a) Pihko, P. M. Angew. Chem. Int. Ed. 2004, 43, 2062.
2. (b) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138.
3. For recent reviews on organocatalysis by proline and proline derivatives, see: (a) List, B. Acc. Chem. Res. 2004, 37, 548.
4. (b) Notz, W.; Tanaka, F.; Barbas, C. F. III. Acc. Chem. Res. 2004, 37, 580.
5. (c) List, B. Tetrahedron 2002, 58, 5573.
6. (a) Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 9662.
7. (b) Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature 2003, 424, 146.
8. (c) McDougal, N. T.; Schaus, S. E. J. Am. Chem. Soc. 2003, 125, 12094.
9. (d) Thadani, A. N.; Stankovic, A. R.; Rawal, V. H. Proc. Natl. Acad. Sci., U.S.A. 2004, 101, 5839.
10. (e) Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804; and references therein.
11. (a) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
12. (b) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
13. (c) Wenzel, A. G.; Jacobsen, E. N. Synlett 2003, 1919.
14. (d) Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102.
15. For a review, see: (a) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
16. (b) For thiourea as ligand in transition metal-catalyzed reactions, see: Yang, D.; Chen, Y.-C.; Zhu, N.-Y. Org. Lett. 2004, 6, 1577; and references therein.
17. (a) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
18. (b) Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625.
19. (c) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.
20. (d) Achiral F-C alkylation with nitroolefin, see: Dessole, G.; Herrera, R. P.; Ricci, A. Synlett 2004, 2374.
21. (a) Sohtome, Y.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Chem. Pharm. Bull. 2004, 52, 477.
22. (b) Sohtome, Y.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2004, 45, 5589.
23. For a review on enantioselective 1,4-addition of thiol to activated olefin, see: (a) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566.
24. (b) For recent examples, see: Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974.
25. (c) Emori, E.; Arai, T.; Sasai, H.; Shibashaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
26. (d) Kanemasa, S.; Oderaotoshi, Y.; Wada, E. J. Am. Chem. Soc. 1999, 121, 8675.
27. (e) Kobayashi, S.; Ogawa, C.; Kawamura, M.; Sugiura, M. Synlett 2001, 983.
28. (f) McDaid, P.; Chen, Y.; Deng, L. Angew. Chem. Int. Ed. 2002, 41, 338.
29. (g) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431.
30. (h) Matsumoto, K.; Watanabe, A.; Uchida, T.; Ogi, K.; Katsuki, T. Tetrahedron Lett. 2004, 45, 2385.
31. (a) For a recent review on asymmetric catalysis with modified cinchona alkaloids, see: Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621.
32. (b) For late examples, see: Zhu, C.; Shen, X.; Nelson, S. G. J. Am. Chem. Soc. 2004, 126, 5352.
33. (c) Li, H.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906.
34. (d) Saaby, S.; Bella, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 8120.
35. (e) Acocella, M. R.; Mancheno, O. G.; Bella, M.; Jørgensen, K. A. J. Org. Chem. 2004, 69, 8165.
36. Brunner, H.; Bügler, J.; Nuber, B. Tetrahedron: Asymmetry 1995, 6, 1699.
37. (a) Goodman, S. N.; Jacobsen, E. N. Adv. Synth. Catal. 2002, 344, 953.
38. (b) For enantioselective 1,4-addition with unsaturated imide, see: Sammis, G. M.; Danjo, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 9928; and references therein,
39. (c) We failed to get the desired Michael addition product using cinnamoyl-2-oxazolidinone as the receptor.
40. Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217.
41. Kaik, M.; Gawroński, J. Tetrahedron: Asymmetry 2003, 14, 1559.
42. HRMS data of new organocatalysts: 1a, 564.1770 (calcd 564.1782); 1b, 564.1781 (calcd 564.1782); 1f, 501.1853 (calcd 501.1861); 1g, 701.1728 (calcd 701.1734).
43. R= 12.1 min, 75% ee).
44. (a) Okino, T.; Hoashi, Y.; Takemoto, Y. Tetrahedron Lett. 2003, 44, 2817.
45. (b) Wittkopp, A.; Shreiner, P. R. Chem.-Eur. J. 2003, 9, 407.
46. For catalytic asymmetric protonation in Michael additions of thiols, see: (a) Pracejus, V. H.; Wilcke, F.-W.; Hanemann, K. J. Prakt. Chem. 1977, 319, 219.
47. (b) Kumar, A.; Salunkhe, R. V.; Rane, R. A.; Dike, S. Y. J. Chem. Soc., Chem. Commun. 1991, 485; also see ref. 7c.
48. (c) For catalytic protonation of enolate, see: Ishihara, K.; Nakashima, D.; Hiraiwa, Y.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 24; and references therein,
49. (d) Hamashima, Y.; Somei, H.; Shimura, Y.; Tamura, T.; Sodeoka, M. Org. Lett. 2004, 6, 1861.
50. 8c