High turnover frequency observed in catalytic enantioselective additions of enecarbamates and enamides to iminophosphonates

Organic Letters

Volumn 8, Issue 23, 2006, Pages 5333-5335

  Kiyohara, Hiroshi ^a   Matsubara, Ryosuke ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CARBAMATES; CATALYSIS; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS;

EID: 33845236727     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062144+     Document Type: Article

References (38)

1. For turnover acceleration examples by Brønsted acid as an additive, see: (a) Dosa, P. I.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445.
2. (b) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2000, 39, 1650.
3. (c) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536.
4. (d) Wadamoto, M.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 14556.
5. (e) Wada, R.; Shibuguchi, T.; Makino, S.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7687.
6. For reviews on enantioselective α-amino acid synthesis, see: (a) Groger, H. Chem. Rev. 2003, 103, 2795.
7. (b) Burk, M. J. Acc. Chem. Res. 2000, 33, 363.
8. For examples of carbon-phosphorus bond-forming reactions, see: (a) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656.
9. (b) Gröger, H.; Saida, Y.; Arai, S.; Martens, J.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 9291.
10. (c) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089.
11. (d) Schlemminger, I.; Saida, Y.; Gröger, H.; Maison, W.; Durot, N.; Sasai, H.; Shibasaki, M.; Martens, J. J. Org. Chem. 2000, 65, 4818.
12. (e) Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102.
13. (f) Akiyama, T.; Morita, H.; Itoh, J.; Fuchibe, K. Org. Lett. 2005, 7, 2583.
14. (g) Pettersen, D.; Marcolini, M.; Bernardi, L.; Fini, F.; Herrera, R. P.; Sgarzani, V.; Ricci, A. J. Org. Chem. 2006, 71, 6269.
15. For examples of enamide hydrogenation, see: (h) Schöllkopf, U.; Hoppe, I.; Thiele, A. Liebigs Ann. Chem. 1985, 555.
16. Schmidt, U.; Oehme, G.; Krause, H. W. Synth. Commun. 1996, 26, 777.
17. (g) Schmidt, U.; Krause, H. W.; Oehme, G.; Michalik, M.; Fischer, C. Chirality 1998, 10, 564.
18. (k) Burk, M. J.; Stammers, T. A.; Straub, J. A. Org. Lett. 1999, 1, 387.
19. For examples of carbon- carbon bond-forming reactions, see: (l) Sawamura, M.; Ito, Y.; Hayashi, T. Tetrahedron Lett. 1989, 30, 2247.
20. Kuwano, R.; Nishio, R.; Ito, Y. Org. Lett. 1999, 1, 837.
21. For examples of carbon-nitrogen bond-forming reactions to give quaternary carbon centers, see: (n) Bernardi, L.; Zhuand, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 5772.
22. (o) Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309.
23. See also: (p) Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769.
24. Kobayashi, S.; Kiyohara, H.; Nakamura, Y.; Matsubara, R. J. Am. Chem. Soc. 2004, 126, 6558.
25. For examples of the use of HFIP for turnover acceleration, see: (a) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015.
26. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865.
27. (c) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595.
28. (d) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Wills, M. C. J. Am. Chem. Soc. 2001, 123, 4480.
29. (e) Takita, R.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 4661.
30. (f) Majima, K.; Takita, R.; Okada, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 15837.
31. (a) Matsubara, R.; Nakamura, Y.; Kobayashi, S. Angew. Chem., Int. Ed. 2004, 43, 1679.
32. (b) Matsubara, R.; Nakamura, Y.; Kobayashi, S. Angew. Chem., Int. Ed. 2004, 43, 3258.
33. (c) Matsubara, R.; Vital, P.; Nakamura, Y.; Kiyohara, H.; Kobayashi, S. Tetrahedron 2004, 60, 9769.
34. (d) Fossey, J. S.; Matsubara, R.; Vital, P.; Kobayashi, S. Org. Biomol. Chem. 2005, 3, 2910.
35. (e) Matsubara, R.; Kawai, N.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 3814.
36. After our reports, other groups also used enecarbamates as nucleophiles. See, for example: (f) Terada, M.; Machioka, K.; Sorimachi, K. Angew. Chem., Int. Ed. 2006, 45, 2254.
37. (a) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143.
38. (b) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507.