Highly anti-selective asymmetric nitro-mannich reactions catalyzed by bifunctional amine-thiourea-bearing multiple hydrogen-bonding donors

Journal of the American Chemical Society

Volumn 130, Issue 27, 2008, Pages 8606-8607

  Wang, Chun Jiang ^a   Dong, Xiu Qin ^a   Zhang, Zhi Hai ^a   Xue, Zhi Yong ^a   Teng, Huai Long ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; HYDROGEN; IMINE; NITROALKANE; NITROMETHANE; THIOUREA;

ARTICLE; ASYMMETRIC NITRO MANNICH REACTION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; DIASTEREOISOMER; ELECTRON TRANSPORT; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; MANNICH REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 46949084402     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803538x     Document Type: Article

References (37)

1. For recent advances on this reaction, see: (a) Westermann, B. Angew. Chem., Int. Ed. 2003, 42, 151.
2. (b) Ting, A.; Schaus, S. E. Eur. J. Org. Chem. 2007, 5797.
3. (a) Bernadi, L.; Bonini, B. F.; Capita, I, E.; Dessole, G.; Comes-Franchini, M.; Fochi, M.; Ricci, A. J. Org. Chem. 2004, 69, 8168.
4. (b) Lloyd, D. H.; Nichols, D. E. J. Org. Chem. 1986, 51, 4294.
5. (c) Barrett, A. G. M.; Spilling, C. D. Tetrahedron Lett. 1988, 29, 5733.
6. (d) Sturgess, M. A.; Yarberry, D. J. Tetrahedron Lett. 1993, 34, 4743.
7. (e) Adams, H.; Anderson, J. C.; Peace, S.; Pennell, A. M. K. J. Org. Chem. 1998, 63, 9932.
8. (a) Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017.
9. (b) Foresti, E.; Palmieri, G.; Petrini, M.; Profeta, R. Org. Biomol. Chem. 2003, 1, 4275.
10. (a) Yamada, K.-I.; Harwood, S. J.; Groger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 3504.
11. (b) Yamada, K.-I.; Moll, G.; Shibasaki, M. Synlett 2001, 980.
12. (a) Nishiwaki, N.; Knudsen, K. R.; Gothelf, K. V.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2992.
13. (b) Knudsen, K. R.; Risgaard, T.; Nishiwaki, N.; Gothelf, K. V.; Jørgensen, K. A. J. Am. Chem. Soc. 2001, 123, 5843.
14. (c) Knudsen, K. R.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 1362.
15. (d) Anderson, J. C.; Blake, A. J.; Howell, G. P.; Wilson, C. J. J. Org. Chem. 2005, 70, 549.
16. (e) Anderson, J. C.; Howell, G. P.; Lawrence, R. M.; Wilson, C. J. J. Org. Chem. 2005, 70, 5665.
17. (f) Palomo, C.; Oiarbide, M.; Halder, R.; Laso, A.; Loípez, R. Angew. Chem., Int. Ed. 2006, 45, 117.
18. (g) Trost, B. M.; Lupton, D. W. Org. Lett. 2007, 9, 2023.
19. (h) Gao, F.; Zhu, J.; Tang, J. Y.; Deng, M.; Qian, C. Chirality 2006, 18, 741.
20. (i) Lee, A.; Kim, W.; Lee, J.; Hyeon, T.; Kim, B. M. Tetrahedron: Asymmetry 2004, 15, 2595.
21. (a) Robak, M. T.; Trincado, M.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 15110.
22. (b) Yoon, T. P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 466.
23. (c) Palomo, C.; Oiarbide, M.; Halder, R.; Laso, A.; Lopez, R. Angew. Chem., Int. Ed. 2006, 45, 117.
24. (d) Wang, C.; Zhou, Z.; Tang, C. Org. Lett. 2008, 10, 1707.
25. (e) Okino, T.; Nakamura, A.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625.
26. (f) Xu, X. N.; Furukawa, T.; Okino, T.; Miyabe, H.; Takemoto, Y. Chem. - Eur. J. 2006, 12, 466.
27. (a) Nugent, B. M.; Yoder, R. A.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 3418.
28. (b) Singh, A.; Yoder, R. A.; Shen, B.; Johnston, J. N. J. Am. Chem. Soc. 2007, 129, 3466.
29. (c) Singh, A.; Johnston, J. N. J. Am. Chem. Soc. 2008, 130, 5866.
30. (a) Palomo, C.; Oiarbide, M.; Laso, A.; Loípez, R. J. Am. Chem. Soc. 2005, 127, 17622.
31. (b) Fini, F.; Sgarzani, V.; Pettersen, D.; Herrera, R. P.; Bernadi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44, 7975.
32. (c) Bernardi, L.; Fini, F.; Herrera, R. P.; Ricci, A.; Sgarzani, V. Tetrahedron 2006, 62, 375.
33. (d) Bode, C. M.; Ting, A.; Schaus, S. E. Tetrahedron 2006, 62, 11499.
34. Handa, S.; Gnanadesikan, V.; Matsunag, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 4900.
35. Wang, C.-J.; Zhang, Z.-H.; Dong, X.-Q.; Wu, X.-J. Chem. Commun. 2008, 1431.
36. β-nitroamine 5 was named as anti-isomer according to Shibasaki's paper.
37. The absolute configurations of the known products were assigned by HPLC and optical rotation comparisons with the reported data (see refs 6b, 6d, and Supporting Information), and those of other adducts were deduced on the basis of these results.