Highly diastereoselective asymmetric Mannich reactions of 1,3-dicarbonyls with acyl imines

Organic Letters

Volumn 8, Issue 10, 2006, Pages 2003-2006

  Ting, Amal ^a   Lou, Sha ^a   Schaus, Scott E ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CINCHONA ALKALOID; IMINE; KETONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CINCHONA ALKALOIDS; CRYSTALLOGRAPHY, X-RAY; IMINES; KETONES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33744733390     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060304b     Document Type: Article

References (58)

1. (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517.
2. (b) Moreno-Manas, M.; Trepat, E.; Sebastian, R. M.; Vallribera, A. Tetrahedron: Asymmetry 1999, 10, 4211.
3. (c) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591.
4. (d) Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784.
5. (e) Trost, B. M.; Dogra, K. J. Am. Chem. Soc. 2002, 124, 7256.
6. (f) Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688.
7. (g) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139.
8. (h) Berkowitz, D. B.; Salud-Bea, R.; Jahng, W.-J. Org. Lett. 2004, 6, 1821.
9. (a) Barta, N. S.; Brode, A.; Stille, J. R. J. Am. Chem. Soc. 1994, 116, 6201.
10. (b) Liu, M.; Sibi, M. P. Tetrahedron 2002 58, 7991.
11. (c) Jang, D. O.; Kim, D. D.; Pyun, D. K.; Beak, P. Org. Lett. 2003, 5, 4155.
12. (d) Sewald, N. Angew. Chem., Int. Ed. 2003, 42, 5794.
13. (e) Ma, J.-A. Angew. Chem., Int. Ed. 2003, 42, 4290.
14. (f) Hamashima, Y.; Sasamoto, N.; Hotta, D.; Somei, H.; Umebayashi, N.; Sodeoka, S. Angew. Chem., Int. Ed. 2005, 44, 1525.
15. (a) Potter, E. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 11516.
16. (b) Sadowsky, J. D.; Schmitt, M. A.; Lee, H.-S.; Umezawa, N.; Wang, S.; Tomita, Y.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 11966.
17. (c) Schmitt, M. A.; Choi, S. H.; Guzei, I. A.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 13130.
18. (d) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
19. (a) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2014.
20. (b) Avenoza, A.; Busto, J. H.; Corzana, F.; Jimènez-Osès, G.; Peregrina, J. M. Chem. Commun. 2004, 980.
21. (c) Seebach, D.; Lelais, G. Biopolymers 2004, 76, 206.
22. (d) Fuller, A. A.; Chen, B.; Minter, A. R.; Mapp, A. K. J. Am. Chem. Soc. 2005, 127, 5376.
23. (e) Ooi, T.; Miki, T.; Maruoka, K. Org. Lett. 2005, 7, 191.
24. (a) Schirlin, D.; Gerhart, F. J. Med. Chem. 1988, 31, 30.
25. (b) Karle, I. L.; Kaul, R.; Rao, B. R.; Raghothama, S.; Balaram, P. J. Am. Chem. Soc. 1997, 119, 12048.
26. (c) Nikolaus, N.; Westermann, B.; Arend, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
27. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
28. (e) Jacobsen, E. N.; Vachal, P. Org. Lett. 2000, 2, 867.
29. (f) Kawabata, T.; Kawakami, S.; Majumdar, S. J. Am. Chem. Soc. 2003, 125, 13012.
30. (g) Liu, X.; Hartwig, J. F. Org. Lett. 2003, 5, 1915.
31. (h) Zhuang, W.; Saaby, S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 4476.
32. (i) Suri, J. T.; Steiner, D. D.; Barbas, C. F., III. Org. Lett. 2005, 7, 3885.
33. (a) Enantioselective Syntheses of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
34. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
35. (c) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842.
36. (d) Uraguchi, T.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
37. (e) Poulsen, T. B.; Alemparte, C.; Saaby, S.; Bella, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 2896.
38. Lou, S.; Taoka, B.; Ting, A.; Schaus, S. E. J. Am. Chem. Soc. 2005, 127, 11256.
39. (a) Marigo, M.; Kjaersgaard, A.; Juhl, K.; Gathergood, N.; Jørgensen, K. A. Chem.-Eur. J. 2003, 9, 2359.
40. (b) Saaby, S.; Nakama, K.; Liu, M. A.; Hazell, R. G.; Jørgensen, K. A. Chem.-Eur. J. 2003, 9, 6145.
41. (c) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, 6, 2507.
42. (d) Tillman, A. L.; Ye, J.; Dixon, D. J. Chem. Commun. 2006, 11, 1191.
43. For the preparation of 7a-d and 8a,b, see: Vidal, J.; Damestoy, S.; Guy, L.; Hannachi, J.-C.; Aubry, A.; Collet, A. Chem.-Eur. J. 1997, 3, 1691. For the preparation of 17a,b, see Supporting Information.
44. Products yielded from dihydroquinidine-catalyzed reactions have the same stereochemistry to reactions catalyzed by cinchonine.
45. Karlsson, S.; Högber, H.-E. Eur. J. Org. Chem. 2003, 2782. See Supporting Information for the full analysis.
46. (a) Brown, H. C.; Brewster, J. H.; Shechter, H. J. Am. Chem. Soc. 1954, 76, 467.
47. (b) Iglesias, E. New J. Chem. 2002, 26, 1352.
48. Molecular Operating Environment, 2004.03; Chemical Computing Group: Montreal, Quebec, Canada.
49. Halgren, T. A. J. Compul. Chem. 1996, 17, 519.
50. (a) France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Chem. Rev. 2003, 103, 2985.
51. (b) Li, H.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906.
52. (c) Tian, S.-T.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621.
53. (d) Liu, X.; Li, H.; Deng, L. Org. Lett. 2005, 7, 167.
54. Similar models have been proposed for diastereoselective β-keto ester additions to nitroolefins: (a) Li, H.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906.
55. (b) Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2005, 44, 105.
56. (c) McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367.
57. For conformational studies of cinchona alkaloid-catalyzed reactions, see: Cortez, G. S.; Oh, S. H.; Romo, D. Synthesis 2001, 1731.
58. (b) Taggi, A. E.; Hafez, A. M.; Dudding, T.; Lectka, T. Tetrahedron 2002, 58, 8351.