Enantioselective synthesis of stimulus-responsive amino acid via asymmetric α-amination of aldehyde

Tetrahedron

Volumn 66, Issue 37, 2010, Pages 7367-7372

  Shigenaga, Akira ^a   Yamamoto, Jun ^a   Nishioka, Naomi ^a   Otaka, Akira ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Asymmetric amination; Organocatalyst; Peptide bond cleavage; Stimulus responsive; UV responsive

Indexed keywords

ALDEHYDE; AMINO ACID; PEPTIDE;

AMINATION; ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; SOLID PHASE SYNTHESIS; SYNTHESIS;

EID: 77955847817     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.07.033     Document Type: Article

References (66)

1. H. Li, J.-M. Hah, and D.S. Lawrence J. Am. Chem. Soc. 130 2008 10474 10475
2. M. Toebes, M. Coccoris, A. Bins, B. Rodenko, R. Gomez, N.J. Nieuwkoop, W.v.d. Kasteele, G.F. Rimmelzwaan, J.B.A.G. Haanen, and T.N.M. Schumacher Nature Med. 12 2006 246 251
3. L.L. Parker, J.W. Kurutz, S.B.H. Kent, and S.J. Kron Angew. Chem., Int. Ed. 45 2006 6322 6325
4. Y. Sohma, and Y. Kiso ChemBioChem 7 2006 1549 1557
5. J.-P. Pellois, and T.W. Muir Angew. Chem., Int. Ed. 44 2005 5713 5717
6. S. Dos Santos, A. Chandravarkar, B. Mandal, R. Mimna, K. Murat, L. Saucede, P. Tella, G. Tuchscherer, and M. Mutter J. Am. Chem. Soc. 127 2005 11888 11889
7. M. Endo, K. Nakayama, Y. Kaida, and T. Majima Angew. Chem., Int. Ed. 43 2004 5643 5645
8. C.J. Bosques, and B. Imperiali J. Am. Chem. Soc. 125 2003 7530 7531
9. P.M. England, H.A. Lester, N. Davidson, and D.A. Dougherty Proc. Natl. Acad. Sci. U.S.A. 94 1997 11025 11030
10. C. Renner, and L. Moroder ChemBioChem 7 2006 868 878, and references therein
11. A. Shigenaga, J. Yamamoto, Y. Sumikawa, T. Furuta, and A. Otaka Tetrahedron Lett. 51 2010 2868 2871
12. A. Shigenaga, J. Yamamoto, H. Hirakawa, K. Ogura, N. Maeda, K. Morishita, and A. Otaka Tetrahedron Lett. 51 2010 2525 2528
13. A. Shigenaga, J. Yamamoto, H. Hirakawa, K. Yamaguchi, and A. Otaka Tetrahedron 65 2009 2212 2216
14. A. Shigenaga, D. Tsuji, N. Nishioka, S. Tsuda, K. Itoh, and A. Otaka ChemBioChem 8 2007 1929 1931
15. M.E. Jung, and G. Piizzi Chem. Rev. 105 2005 1735 1766, and references therein
16. K.L. Amsberry, and R.T. Borchardt J. Org. Chem. 55 1990 5867 5877
17. M. Caswell, and G.L. Schmir J. Am. Chem. Soc. 102 1980 4815 4821
18. S. Milstien, and L.A. Cohen J. Am. Chem. Soc. 94 1972 9158 9165
19. R.T. Borchardt, and L.A. Cohen J. Am. Chem. Soc. 94 1972 9166 9174
20. S. Milstien, and L.A. Cohen Proc. Natl. Acad. Sci. U.S.A. 67 1970 1143 1147
21. Recent reviews:
22. S. Bertelsen, and K.A. Jørgensen Chem. Soc. Rev. 38 2009 2178 2189
23. S. Mukherjee, J.W. Yang, S. Hoffmann, and B. List Chem. Rev. 107 2007 5471 5569
24. A. Erkkilä, I. Majander, and P.M. Pihko Chem. Rev. 107 2007 5416 5470
25. W. Notz, F. Tanaka, and C.F. Barbas III Acc. Chem. Res. 37 2004 580 591
26. R.O. Duthaler Angew. Chem., Int. Ed. 42 2003 975 978
27. D.G. Blackmond, A. Moran, M. Hughes, and A. Armstrong J. Am. Chem. Soc. 132 2010 7598 9599
28. B. Simmons, A.M. Walji, and D.W.C. MacMillan Angew. Chem., Int. Ed. 48 2009 4349 4353
29. A.-N. Alba, X. Companyo, A. Moyano, and R. Rios Chem. - Eur. J. 15 2009 7035 7038
30. C.E. Hartmanna, P.J. Grossa, M. Niegerb, and S. Bräse Org. Biomol. Chem. 7 2009 5059 5062
31. K. Makino, S. Kubota, S. Hara, M. Sakaguchi, A. Hamajima, and Y. Hamada Tetrahedron 65 2009 9468 9473
32. A. Nuzzi, A. Massi, and A. Dondoni Org. Lett. 10 2008 4485 4488
33. S. George, G.S. Suryavanshi, and A. Sudalai Tetrahedron Lett. 49 2008 6791 6793
34. A. Lim, J.H. Choi, and J. Tae Tetrahedron Lett. 49 2008 4882 4885
35. T. Baumann, H. Vogt, and S. Bräse Eur. J. Org. Chem. 2007 266 282
36. S.K. Talluri, and A. Sudalai Tetrahedron 63 2007 9758 9763
37. S. Umbreen, M. Brockhaus, H. Ehrenberg, and B. Schmidt Eur. J. Org. Chem. 2006 4585 4595
38. S.P. Kotkar, and A. Sudalai Tetrahedron: Asymmetry 17 2006 1738 1742
39. W. Miao, W. Xu, Z. Zhang, R. Ma, S.-H. Chen, and G. Li Tetrahedron Lett. 47 2006 6835 6837
40. J.T. Suri, D.D. Steiner, and C.F. Barbas III Org. Lett. 7 2005 3885 3888
41. H. Iwamura, S.P. Mathew, and D.G. Blackmond J. Am. Chem. Soc. 126 2004 11770 11771
42. H. Iwamura, D.H. Wells Jr., S.P. Mathew, M. Klussmann, A. Armstrong, and D.G. Blackmond J. Am. Chem. Soc. 126 2004 16312 16313
43. N.S. Chowdari, D.B. Ramachary, and C.F. Barbas III Org. Lett. 5 2003 1685 1688
44. A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, and K.A. Jørgensen Angew. Chem., Int. Ed. 41 2002 1790 1793
45. B. List J. Am. Chem. Soc. 124 2002 5656 5657
46. T. Baumann, M. Bächle, C. Hartmann, and S. Bräse Eur. J. Org. Chem. 2008 2207 2212
47. R. Ait-Youcef, K. Sbargoud, X. Moreau, and C. Greck Synlett 2009 3007 3010
48. Y. Nishikawa, M. Kitajima, N. Kogure, and H. Takayama Tetrahedron 65 2009 1608 1617
49. D. Kalch, N. De Rycke, X. Moreau, and C. Greck Tetrahedron Lett. 50 2009 492 494
50. Y. Hayashi, S. Aratake, Y. Imai, K. Hibino, Q.-Y. Chen, J. Yamaguchi, and T. Uchimaru Chem. - Asian J. 3 2008 225 232
51. Y. Nishikawa, M. Kitajima, and H. Takayama Org. Lett. 10 2008 1987 1990
52. H. Jiang, J.B. Nielsen, and K.A. Jørgensen Chem. - Eur. J. 13 2007 9068 9075
53. C. Thomassigny, D. Prim, and C. Greck Tetrahedron Lett. 47 2006 1117 1119
54. J. Franzen, M. Marigo, D. Fielenbach, T.C. Wabnitz, A. Kjærsgaard, and K.A. Jørgensen J. Am. Chem. Soc. 127 2005 18296 18304
55. M. Marigo, T. Schulte, J. Franzen, and K.A. Jørgensen J. Am. Chem. Soc. 127 2005 15710 15711
56. P. Kotrusz, S. Alemayehu, S. Toma, H.-G. Schmalz, and A. Adler Eur. J. Org. Chem. 2005 4904 4911
57. N.S. Chowdari, and C.F. Barbas III Org. Lett. 7 2005 867 870
58. N. Dahlin, A. Bøgevig, and H. Adolfsson Adv. Synth. Catal. 346 2004 1101 1105
59. Y. Henmi, K. Makino, Y. Yoshitomi, O. Hara, and Y. Hamada Tetrahedron: Asymmetry 15 2004 3477 3481
60. H. Vogta, S. Vanderheidena, and S. Bräse Chem. Commun. 2003 2448 2449
61. Preparation of sulfonamide 7 and tetrazole 9, see: A.J.J. Cobb, D.M. Shaw, D.A. Longbottom, J.B. Gold, and S.V. Ley Org. Biomol. Chem. 3 2005 84 96 Toluene solution of silyl ether 8 was purchased from SIGMA-ALDRICH
62. T. Kusumi, T. Ooi, Y. Ohkubo, and T. Yabuuchi Bull. Chem. Soc. Jpn. 79 2006 965 980, and references therein
63. T. Kusumi, T. Fukushima, I. Ohtani, and H. Kakisawa Tetrahedron Lett. 32 1991 2939 2942
64. I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa J. Am. Chem. Soc. 113 1991 4092 4096
65. K. Hattori, H. Sajiki, and K. Hirota Tetrahedron Lett. 41 2000 5711 5714
66. E.J. Corey, and G. Schmidt Tetrahedron Lett. 20 1979 399 402