Modified 3-hydroxypipecolic acid derivatives as an organocatalyst

Heterocycles

Volumn 77, Issue 1, 2009, Pages 635-644

  Oshimura, Yuichi ^a   Ohara, Chiaki ^a   Miyagawa, Tatsunori ^a   Takahata, Hiroki ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Amino Acid; Asymmetric Reaction; Mannich Reaction; Organocatalyst; Pipecolic Acid

Indexed keywords

EID: 65549142973     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(F)61     Document Type: Article

References (33)

1. Selected reviews for organocatalysis. Dondoni A., and Massi A. Angw. Chem. Int. Ed. 47 (2008) 4638
2. Guillena G., Nájera C., and Ramón D.J. Tetrahedron: Asymmetry 18 (2007) 2249
3. Mukherjee S., Yang J.W., Hoffmann S., and List B. Chem. Rev. 107 (2007) 5471
4. Notz W., Tanaka F., and Barabas III C.F. Acc. Chem. Res. 37 (2004) 580
5. Dalko P.I., and Moisan L. Angw. Chem. Int. Ed. 43 (2004) 5138
6. Gaunt M.J., Johansson C.C.C., McNally A., and Vo N.T. Drug Discov. Today 12 (2007) 8
7. Kotsuki H., Ikishima H., and Okuyama A. Heterocycles 75 (2008) 493
8. Kotsuki H., Ikishima H., and Okuyama A. Heterocycles 75 (2008) 757
9. List B., Lerner R.A., and Barabas III C.F. J. Am. Chem. Soc. 122 (2000) 2395
10. Sakthivel K., Notz W., Bui T., and Barabas III C.F. J. Am. Chem. Soc. 123 (2001) 5260
11. Notz W., and List B. J. Am. Chem. Soc. 122 (2000) 7386
12. List B., Pojarliev P., Biller W.T., and Martin H.J. J. Am. Chem. Soc. 124 (2002) 827
13. Bui T., and Barbas III C.F. Tetrahedron Lett. 41 (2000) 6951
14. List B., Pojarliev H.J., and Martin. Org. Lett. 3 (2001) 2423
15. Thayumanavan R., Dhevalapally B., Sakthivel K., Tanaka F., and Barbas III C.F. Tetrahedron Lett. 43 (2002) 3817
16. Inomata K., Barragué M., and Paquette L.A. J. Org. Chem. 70 (2005) 533
17. Enders D., Hüttl M.R.M., Grondai C., and Raabe G. Nature 441 (2006) 861
18. Torii H., Nakadai M., Ishihara K., Saito S., and Yamamoto H. Angw. Chem. Int. Ed. 43 (2004) 1983
19. Aroyan C.E., Vasbinder M.M., and Miller S.J. Org. Lett. 7 (2005) 3849
20. Cheong P.H.-Y., Zhang H., Thayumanavan R., Tanaka F., Houk K.N., and Barbas III C.F. Org. Lett. 8 (2006) 811
21. Imahori T., Ojima H., Tateyama H., Mihara Y., and Takahata H. Tetrahedron Lett. 49 (2008) 265
22. Mihara Y., Ojima H., Imahori T., Yoshimura Y., Ouchi H., and Takahata H. Heterocycles 72 (2007) 633
23. Takahata H., Suto Y., Kato E., Yoshimura Y., and Ouchi H. Adv. Syn. Cat. 349 (2007) 685
24. Ouchi H., Mihara Y., and Takahata H. J. Org. Chem. 70 (2005) 5207
25. Asano N., Ikeda K., Yu L., Kato A., Takebayashi K., Adachi I., Kato I., Ouchi H., Takahata H., and Fleet G.W.J. Tetrahedron: Asymmetry 16 (2005) 223
26. Kato A., Kato N., Kano E., Adachi I., Ikeda K., Yu L., Okamoto T., Banba Y., Ouchi H., Takahata H., and Asano N. J. Med. Chem. 48 (2005) 2036
27. Ouchi H., Mihara Y., Watanabe H., and Takahata H. Tetrahedron Lett. 45 (2004) 7053
28. Takahata H., Banba Y., Sasatani M., Nemoto H., Kato A., and Adachi I. Tetrahedron 60 (2004) 8199
29. Takahata H., Banba Y., Ouchi H., and Nemoto H. Org. Lett. 5 (2003) 2527
30. Banba Y., Abe C., Nemoto H., Kato A., Adachi I., and Takahata H. Tetrahedron: Asymmetry 12 (2001) 817
31. Ohara C., Takahashi R., Miyagawa T., Yoshimura Y., Kato A., Adachi I., and Takahata H. Bioorg. Med. Chem. Lett. 18 (2008) 1810
32. Yoshimura Y., Ohara C., Imahori T., Saito Y., Kato A., Miyauchi S., Adachi I., and Takahata H. Bioorg. Med. Chem. (2008) in press and references for the synthesis of 3-hydroxypipecolic acids cited therein
33. The absolute stereochemistries of the Mannich products were determined by the comparison of retention times of chiral HPLC analysis with the data shown in ref 9b.