Amine-salt-controlled, catalytic asymmetric conjugate addition of various amines and asymmetric protonation

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1861-1864

  Hamashima, Yoshitaka ^a   Somei, Hidenori ^a   Shimura, Yuta ^a   Tamura, Toshihiro ^a   Sodeoka, Mikiko ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BETA AMINO ACID; PALLADIUM; SODIUM CHLORIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; PROTON TRANSPORT;

EID: 2942629592     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0493711     Document Type: Article

References (40)

1. (a) Juaristi, E., Ed. Enantioselective Synthesis of β-Amino Acids; Wiley-VHC: New York, 1997.
2. (b) Magriotis, P. A. Angew. Chem., Int. Ed. 2001, 40, 4377-4379.
3. (c) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991-8035.
4. (d) Ma, J.-A. Angew. Chem., Int. Ed. 2003, 42, 4290-4299.
5. (e) Sewald, N. Angew. Chem., Int. Ed. 2003, 42, 5794-5795.
6. (a) Falborg, L.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 1996, 2823-2826.
7. (b) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615-6616.
8. (c) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959-8960.
9. (d) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635-3638.
10. (e) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134-2136.
11. (f) Sibi, M. P.; Prabagaran, N.; Ghorpade, S. G.; Jasperse, C. P. J. Am. Chem. Soc. 2003, 125, 11796-11797. For a recent example in the case of enones: (g) Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 16178-16179 and references therein.
12. (f) Sibi, M. P.; Prabagaran, N.; Ghorpade, S. G.; Jasperse, C. P. J. Am. Chem. Soc. 2003, 125, 11796-11797. For a recent example in the case of enones: (g) Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 16178-16179 and references therein.
13. Paradisi, M. P.; Romeo, A. J. Chem. Soc., Perkin Trans, 1 1977, 596-600.
14. (a) Zhuang, W.; Hazell, R. G.; Jørgensen, K. A. Chem. Commun. 2001, 1240-1241.
15. (b) Fadini, L.; Togni, A. Chem. Commun. 2003, 30-31.
16. (c) Li, K.; Hii, K. K. Chem. Commun. 2003, 1132-1133.
17. 3 using a chiral ether ligand: Doi, H.; Sakai, T.; Iguchi. M.; Yamada, K.; Tomioka, K. J. Am. Chem. Soc. 2003, 125, 2886-2887.
18. (a) Sodeoka, M.; Ohrai, M.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
19. (b) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466.
20. (c) Sodeoka, M.; Shibasaki, M. Pure Appl. Chem. 1998, 70, 411-414.
21. (d) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475.
22. (e) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450-5458.
23. (f) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
24. (g) Hamashima, Y.; Yagi, K.; Takano, H.; Tamás, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530-14531.
25. (h) Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M. Org. Lett. 2003, 5, 3225-3228.
26. Unpublished results. See Supporting Information.
27. Li, K.; Cheng, X.; Hii, K. K. Eur. J. Org. Chem. 2004, 959-964. This paper appeared during the preparation of our manuscript.
28. AcOH, HCl, and MsOH gave less satisfactory results.
29. An interesting proton effect was reported previously: Seligson, A. L.; Trogler, W. C. Organometallics 1993, 12, 744-751.
30. A trace amount of the product was formed in toluene, probably because the salt was not dissolved.
31. Recently, Spencer et al. reported that the proton itself can be an active achiral catalyst for aza-Michael reaction. See: Wabnitz, T. C.; Yu, J.-Q.; Spencer, J. B. Chem. Eur. J. 2004, 10, 484-493. In contrast, high enantioselectivity was observed under our optimized conditions even in the presence of a stoichiometric amount of proton source (Table 1, entry 5).
32. 2, gave the pure product 5aa. The ee of the product was determined by chiral HPLC.
33. See Supporting Information for details.
34. Generally, a tedious anhydrous condition is required to avoid hydrolysis of the metal catalyst. See ref 12.
35. In ref 5, a catalytic amount of chiral ether ligand (0.3 equiv) afforded the product in 75% yield and 70% ee (-78°C, 17 h). For substoichiometric reaction (50 mol %): Sundararajan, G.; Prabagaran, N. Org. Lett. 2001, 3, 389-392.
36. A partially successful example was reported in ref 4b. The reaction of methacrylonitrile with morpholine afforded the corresponding product in 69% ee.
37. Recent examples of catalytic enantioselctive protonation of transient metal enolate in Michael addition: (a) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (b) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440-442. (c) Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719-723. Radical-based reaction: (d) Sibi, M.; Patil, K. Angew. Chem., Int. Ed. 2004, 43, 1235-1238.
38. Recent examples of catalytic enantioselctive protonation of transient metal enolate in Michael addition: (a) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (b) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440-442. (c) Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719-723. Radical-based reaction: (d) Sibi, M.; Patil, K. Angew. Chem., Int. Ed. 2004, 43, 1235-1238.
39. Recent examples of catalytic enantioselctive protonation of transient metal enolate in Michael addition: (a) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (b) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440-442. (c) Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719-723. Radical-based reaction: (d) Sibi, M.; Patil, K. Angew. Chem., Int. Ed. 2004, 43, 1235-1238.
40. Recent examples of catalytic enantioselctive protonation of transient metal enolate in Michael addition: (a) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (b) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440-442. (c) Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719-723. Radical-based reaction: (d) Sibi, M.; Patil, K. Angew. Chem., Int. Ed. 2004, 43, 1235-1238.