Asymmetric amination of cyclic β-keto esters catalyzed by amine-thiourea bearing multiple hydrogen bonding donors

5. For selected reviews of organocatalysis, see: (a) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2001, 40, 3726. (b) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138. (c) Acc. Chem. Res. 2004, 37, 487. Special issue on organocatalysis. (d) Berkessel, A.; Gröger, H.; Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH: Weinheim 2004. (e) Seayad J.; List, B. Org. Biomol. Chem. 2005, 3, 719. (f) Dondoni, A.; Massi, A. Angew. Chem. Int. Ed. 2008, 47, 4638. 6. Pihko, P. M.; Pohjakallio, A. Synlett 2004, 12, 2115. 7. (a) Saaby, S.; Bella, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 8120. (b) Liu, X.; Li, H.; Deng, L. Org. Lett. 2005, 7, 167. For asymmetric amination of aldehydes, ketones, .- keto esters and alkylidene cyanoacetates, see: (c) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (d) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2002, 41, 1790. (e) Vogt, H.; Vanderheiden, S.; Bräse, S. Chem. Commun. 2003, 2448. (f) Iwamura, H.; Mathew, S. P.; Blackmond, D. G. J. Am. Chem. Soc. 2004, 126, 11770. (g) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (h) Juhl, K.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420. (i) Poulsen, T. B.; Alemparte, C.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 11614. (j) Guo, H.-M.; Cheng, L.; Cun, L.-F.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.- Z. Chem. Commun. 2006, 429. (k) Liu, T.-Y.; Cui, H.-L.; Zhang, Y.; Jiang, K.; Du, W.; He, Z.-Q.; Chen, Y.-C. Org. Lett. 2007 9, 3671. 8. Xu, X.; Yabuta, T.; Yuan, P.; Takemoto, Y. Synlett 2006, 137. 9. (a) Terada, M.; Nakano, M.; Ube, H. J. Am. Chem. Soc. 2006, 128, 16044. (b) He, R.; Wang, X.; Hashimoto, T.; Maruoka, K. Angew. Chem. Int. Ed. 2008, 47, 9466. 10. (a) Wang, C.-J.; Zhang, Z.-H.; Dong, X.-Q.; Wu, X.-J. Chem. Comm. 2008, 1431. (b) Zhang, Z.-H.; Dong, X.-Q.;Chen, D; Wang, C.-J. Chem.-Eur. J. 2008, 14, 8780. (c) Wang, C.-J.; Dong, X.-Q.; Zhang, Z.-H.; Xue, Z.-Y.; Teng, H.-L. J. Am. Chem. Soc. 2008, 130, 8606. (d) Dong, X.-Q.; Teng, H.-L.; Wang, C.-J. Org. Lett. 2009, 11, 1265. 11. This was probably caused by the unstability of the amine-thiourea catalyst under the reaction condition, which was also observed by Takemoto et al, see Ref. 8.