(S)-Indoline-3-Carboxylic Acid: A New Organocatalyst for the Anti Mannich-Type Reaction

ChemCatChem

Volumn 2, Issue 5, 2010, Pages 505-508

  Pietruszka, Jörg ^a   Simon, Robert Christian ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Hydrolases; Kinetic resolution; Mannich reaction; Organocatalysis; Stereoselectivity

Indexed keywords

EID: 77957109029     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201000041     Document Type: Article

References (67)

1. C. Mannich, W. Krösche, Arch. Pharm. 1912, 250, 647-667.
2. A. Córdova, Acc. Chem. Res. 2004, 37, 102-112;
3. A. E. Taggi, A. M. Hafez, T. Lecta, Acc. Chem. Res. 2003, 36, 10-19.
4. J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg, F. P. J. T. Rutjes, Chem. Soc. Rev. 2008, 37, 29-41;
5. A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797-5815;
6. M. M. B. Marques, Angew. Chem. 2006, 118, 356-360
7. M. M. B. Marques, Angew. Chem. Int. Ed. 2006, 45, 348-352.
8. For general reviews on organocatalysis see.
9. P. I. Dalko in Enantioselective Organocatalysis: Reactions and Experimental Procedures, Vol. 1, Wiley-VCH, Weinheim, 2007;
10. S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178-2189;
11. M. J. Gaunt, C. C. C. Johansson, A. Mc Nally, N. T. Vo, Drug Discovery Today 2007, 12, 8-27;
12. H. Pellissier, Tetrahedron 2007, 63, 9267-9331;
13. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569;
14. W. Notz, F. Tanaka, C. F. Barbas III., Acc. Chem. Res. 2004, 37, 580-591;
15. P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248-5286
16. P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138-5175;
17. M. Bella, T. Gasperi, Synthesis 2009, 1583-1614;
18. A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716-4739
19. A. Dondoni, A. Massi, Angew. Chem. Int. Ed. 2008, 47, 4638-4660;
20. J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719-724.
21. B. List, Chem. Rev. 2007, 107, 5413-5415.
22. B. List, Tetrahedron 2002, 58, 5573-5590;
23. B. List, Synlett 2001, 1675-1686.
24. W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III., J. Org. Chem. 2003, 68, 9624-9634;
25. Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805-3808; Angew. Chem. Int. Ed. 2003, 42, 3677-3680.
26. Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai.
27. A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843;
28. A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III., J. Am. Chem. Soc. 2002, 124, 1866-1867;
29. S. Fustero, F. Mojarrad, M. D. P. Carriòn, J. F. Sanz-Cervera, J. L. Aceña, Eur. J. Org. Chem. 2009, 5208-5214.
30. A. J. A. Cobb, D. M. Shaw, S. V. Ley, Synlett 2004, 0558-0560;
31. A. J. A. Cobb, D. M. Shaw, D. A. Longbottom, J. B. Gold, S. V. Ley, Org. Biomol. Chem. 2005, 3, 84-96;
32. W. Wang, J. Wang, H. Li, Tetrahedron Lett. 2004, 45, 7243-7246.
33. A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 7749-7752.
34. For recent examples see.
35. H. Zhang, Y. Chuan, Z. Li, Y. Peng, Adv. Synth. Catal. 2009, 351, 2288-2294;
36. C. Gianelli, L. Sambri, A. Carlone, G. Bartoli, P. Melchiorre, Angew. Chem. 2008, 120, 8828-8830 Angew. Chem. Int. Ed. 2008, 47, 8700-8702;
37. C. Gianelli, L. Sambri, A. Carlone, G. Bartoli, P. Melchiorre, Angew. Chem. Int. Ed. 2008, 47, 8700-8702;
38. P. Dziedzic, A. Córdova, Tetrahedron: Asymmetry 2007, 18, 1033-1037;
39. T. Kano, Y. Yamaguchi, O. Tokuda, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 16408-16409;
40. I. Ibrahem, A. Córdova, Chem. Commun. 2006, 1760-1762.
41. T. Kano, Y. Hato, A. Yamamoto, K. Maruoka, Tetrahedron 2008, 64, 1197-1203;
42. M. Pouliquen, J. Blanchet, M. Lasne, J. Rouden, Org. Lett. 2008, 10, 1029-1032.
43. S. Mitsumori, H. Zhang, P. H. Cheong, K. N. Houk, F. Tanaka, C. F. Barbas III., J. Am. Chem. Soc. 2006, 128, 1040-1041.
44. H. Zhang, M. Mifsud, F. Tanaka, C. F. Barbas III., J. Am. Chem. Soc. 2006, 128, 9630-9631;
45. H. Zhang, S. Mitsumori, N. Utsumi, M. Imai, N. Garcia-Delgado, M. Mifsud, K. Albertshofer, P. H. Cheong, K. N. Houk, F. Tanaka, C. F. Barbas III., J. Am. Chem. Soc. 2008, 130, 875-886.
46. A. Armstrong, A. Bhonoah, A. J. P. White, J. Org. Chem. 2009, 74, 5041-5048;
47. A. Fu, H. Li, T. Chu, H. Zou, P. Feng, S. Yuan, Y. Duan, J. Mol. Catal., A 2009, 314, 1-9.
48. D. Seebach, A. K. Beck, D. N. Badine, M. Limbach, A. Eschenmoser, A. M. Treasurywala, R. Hobi, Helv. Chim. Acta 2007, 90, 425-471;
49. U. Grošelj, D. Seebach, D. M. Badine, W. B. Schweizer, A. K. Beck, Helv. Chim. Acta 2009, 92, 1225-1259.
50. For some recent examples see.
51. M. Bischop, V. Doum, A. C. M. Nordschild (née Rieche), J. Pietruszka, D. Sandkuhl, Synthesis 2010, 527-537;
52. T. Hausmann, J. Pietruszka, Synlett 2009, 3271-3274;
53. J. Pietruszka, R. C. Simon, Eur. J. Org. Chem. 2009, 3628-3634;
54. T. Fischer, J. Pietruszka, Adv. Synth. Catal. 2007, 349, 1533-1536;
55. J. Pietruszka, A. C. M. Rieche, T. Wilhelm, W. Witt, Adv. Synth. Catal. 2003, 345, 1273-1286.
56. For a detailed investigation on the kinetic resolution of structurally related methyl 2, 3-dihydro-1H-indenecarboxylate see.
57. J. Pietruszka, R. C. Simon, F. Kruska, M. Braun, Eur. J. Org. Chem. 2009, 6217-6224. For a discussion concerning the calculation of E values, see.
58. C. S. Chen, Y. Fujimoto, G. Girdaukas, C. J. Sih, J. Am. Chem. Soc. 1982, 104, 7294-7299;
59. W. Kroutil, A. Kleewein, K. Faber, Tetrahedron: Asymmetry 1997, 8, 3251-3291.
60. General review.
61. G. H. Lee, I. K. Youn, E. B. Choi, H. K. Lee, G. H. Yon, H. C. Yank, C. S. Pak, Curr. Org. Chem. 2004, 8, 1263-1287; Reduction of Boc protected methyl indole-2-carboxylate.
62. M. Kurokawa, T. Sugai, Bull. Chem. Soc. Jpn. 2004, 77, 1021-1025.
63. The protein content in Novo435 was determined to be 2% (wt/wt) of the total mass. For further information please see: F. Secundo, G. Carrera, C. Soregaroli, D. Varinelli, R. Morrone, Biotechnol. Bioeng. 2001, 73, 157-163.
64. D. E. Ward, M. Sales, P. K. Sasmal, J. Org. Chem. 2004, 69, 4808-4815.
65. Recently, the List group disclosed an access to the double Mannich products of acetaldehyde and N-protected imines.
66. C. Chandler, P. Galzerano, A. Michrowska, B. List, Angew. Chem. 2009, 121, 2012-2014
67. C. Chandler, P. Galzerano, A. Michrowska, B. List, Angew. Chem. Int. Ed. 2009, 48, 1978-1980.