Catalytic asymmetric reductive Michael cyclization

Journal of the American Chemical Society

Volumn 127, Issue 43, 2005, Pages 15036-15037

  Yang, Jung Woon ^a   Hechavarria Fonseca, Maria T ^a   List, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; IMINE; KETONE; ORGANIC COMPOUND;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; MICHAEL CYCLIZATION; REDUCTION; SYNTHESIS;

EID: 27544489337     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055735o     Document Type: Article

References (42)

1. For an account on aminocatalysis. see: List, B. Synlett 2001, 1675-1686.
2. For the first enamine catalytic asymmetric intermolecular aldol, Mannich, α-amination, and intramolecular α-alkylation reactions, see:
3. (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396.
4. (b) List, B. J. Am. Chem. Soc. 2000, 122, 9336-9337.
5. List, B. J. Am. Chem. Soc. 2002, 124, 5656-5657.
6. Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451.
7. (e) For an account of our contributions to this area, see: List, B. Acc. Chem, Res. 2004, 37, 548-557. Also see:
8. (f) List, B. Tetrahedron 2002, 58, 5572-5590.
9. (g) Gröger, H.; Wilken, J. Angew. Chem., Int. Ed. 2001, 40, 529-532.
10. (h) Movassaghi, M.; Jacobsen, E. N. Science 2002, 298, 1904.
11. Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799.
12. (j) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580-591.
13. (k) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301-303.
14. Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620-621.
15. Cobb, A. J. A.; Shaw, D. M.; Longbottom. D. A.; Gold, J. B.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 84-96.
16. (n) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369-1371.
17. (o) Allemann, C.; Gordillo, R.; Clemente, F. R.; Cheong, P. H.-Y.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558-569.
18. (p) Enders, D.; Grondal, C.; Vrettou, M.; Raabe, G. Angew. Chem., Int. Ed. 2005, 44, 4079-4083.
19. (q) Sunden, H.; Ibrahem, I.; Erikson, L.; Cordova, A. Angew. Chem., Int. Ed. 2005, 44, 4877-4880.
20. (r) Ishii, T.; Fujioka, S.; Sekihuchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558-9559. For pioneering studies, see:
21. (s) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497.
22. (t) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615-1621.
23. For example, see: (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243-4244.
24. (b) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192-1194.
25. Wilson, R. M.; Jen, W. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005. 127, 11616-11617.
26. Marigo, M.; Franzen, J.; Poulsen, T. B.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 6964-6965.
27. (a) Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 6660-6662.
28. (b) Yang, J. W.; Hechavarria Fonseca, M. T.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2005, 44, 108-110.
29. For an independent study on the same reaction, see: Quellet, S. G.; Tuttle, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 32-33.
30. For copper-catalyzed tandem enone conjugate reduction-alkylations/ aldolizations, see: (a) Lipshutz, B. H.; Chrisman, W.; Noson, K.; Papa, P.; Sclafani, J. A.: Vivian, R. W.; Keith, J. M. Tetrahedron 2000, 56, 2779-2788.
31. (b) Yun, J.; Buchwald, S. J. Org. Lett. 2001, 3, 1129-1131.
32. For example, see: (a) Huddleston, R. R.; Krische, M. J. Synlett 2003. 12-21.
33. (b) Jans, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156-15157.
34. Shibata, I.; Kato, H.; Ishida, T.; Yasuda, M.; Baba, A. Angew. Chem., Int. Ed. 2004, 116, 729-732.
35. For example, see: (a) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528-4529.
36. (b) Nishiyama, H.; Shiomi, T.; Tsuchiya, Y.; Matsuda, I. J. Am. Chem. Soc. 2005, 127, 6972-6973.
37. Lam, H. W.; Joensuu, P. M. Org. Lett. 2005, 7, ASAP.
38. For a catalytic asymmetric tandem Michael addition-HT hydrogenation, see: Guo, R.; Morris, R. H.; Song, D. J. Am. Chem. Soc. 2005, 127, 516-517.
39. Hechavarria Fonseca, M. T.; List. B. Angew. Chem., Int. Ed. 2004, 43, 3958-3960.
40. For intermolecular enamine catalytic Michael additions of aldehydes to enones, see: (a) Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. For significantly improved catalyst systems, see:
41. (b) Peelen, T. J.; Chi, Y.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 11598-11599.
42. Chi, Y.; Gellman, S. H. Org. Lett. 2005, 7, ASAP.