Erratum: Asymmetric mannich reaction of fluorinated ketoesters with a tryptophan-derived bifunctional thiourea catalyst (Angewandte Chemie - International Edition (2009) 48 (7604-7607) DOI: 10.1002/anie.200903635);Asymmetric mannich reaction of fluorinated ketoesters with a tryptophan-derived bifunctional thiourea catalyst

Angewandte Chemie - International Edition

Volumn 48, Issue 41, 2009, Pages 7604-7607

  Han, Xiao ^a   Kwiatkowski, Jacek ^a   Xue, Teng ^a   Huang, Kuo Wei ^a   Lu, Yixin ^a,b  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Asymmetric synthesis; Fluorination; Mannich reaction; Organocatalysis; Quaternary stereocenters; asymmetric synthesis; fluorination; organocatalysis; quaternary stereocenters

Indexed keywords

AMINO ACIDS; CATALYSTS; FLUORINATION; STEREOCHEMISTRY;

ASYMMETRIC SYNTHESIS; BI-FUNCTIONAL CATALYSTS; CHIRAL MOLECULE; MANNICH REACTIONS; ORGANOCATALYSIS; QUATERNARY STEREOCENTERS; STEREOGENIC CENTERS; THIOUREA CATALYSTS;

ENANTIOSELECTIVITY;

ESTER; FLUORINE; KETONE; THIOUREA; TRYPTOPHAN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION;

CATALYSIS; ESTERS; FLUORINE; KETONES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; THIOUREA; TRYPTOPHAN;

EID: 70349995077     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201190021     Document Type: Erratum

References (79)

1. a) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289;
2. b) H. Yamamoto, K. Futatsugi, Angew. Chem. 2005, 117, 1958;
3. Angew. Chem. Int. Ed. 2005, 44, 1924 ;
4. c) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999;
5. d) M. S. Taylor, E. N Jacobsen, Angew. Chem. 2006, 118, 1550;
6. Angew. Chem. Int. Ed. 2006, 45, 1520;
7. e) A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713;
8. f) X. Yu, W Wang, Chem. Asian. J. 2008, 3, 516;
9. g) S. J. Connon, Chem. Commun. 2008, 2499.
10. For reviews on bifunctional catalysts and multiple activation, see: a) H. Steinhagen, G. Helmchen, Angew. Chem. 1996, 108, 2489;
11. Angew. Chem. Int. Ed. Engl. 1996, 35, 2339;
12. b) J. D. Wuest, Acc. Chem. Res. 1999, 32, 81;
13. c) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187;
14. d) J.-A. Ma, D. Cahard, Angew. Chem. 2004, 116, 4666;
15. Angew. Chem. Int. Ed. 2004, 43, 4566;
16. e) K. Muñiz, Angew. Chem. 2005, 117, 6780;
17. Angew. Chem. Int. Ed. 2005,44,6622;
18. f) H. Yamamoto, K. Futatsugi, Angew. Chem. 2005,117, 1958;
19. Angew. Chem. Int. Ed. 2005, 44, 1924.
20. For selected examples, see : a) T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672;
21. b) H. Huang, E. N. Jacobsen, J. Am. Chem. Soc. 2006, 128, 7170;
22. c) M. P. Lalonde, Y. Chen, E. N Jacobsen, Angew. Chem. 2006, 118, 6514;
23. Angew. Chem. Int. Ed. 2006, 45,6366;
24. d) J. Wang, H. Li, X. Yu, L. Zu, W. Wang, Org. Lett. 2005, 7, 4293;
25. e) B.-J. Li, L. Jiang, M. Liu, Y.-C. Chen, L.-S. Ding, Y. Wu, Synlett 2005, 603;
26. f) B. Vakulya, S. Varga, A. Csámpai, T. Soós, Org. Lett. 2005, 7,1967;
27. g) S. H. McCooey, S. J. Connon, Angew. Chem. 2005, 117, 6525;
28. Angew. Chem. Int. Ed. 2005,44,6367;
29. h) J. Ye, D. J. Dixon, P. S. Hynes, Chem. Commun. 2005, 4481.
30. For reviews on primary amino acids and primary amines in asymmetric catalysis, see: a) L.-W Xu, J. Luo, Y. Lu, Chem. Commun. 2009, 1807;
31. b) L.-W Xu, Y. Lu, Org. Biomol. Chem. 2008, 6, 2047;
32. c) F. Peng, Z. Shao, J. Mol. Catal. A 2008, 285, 1; for relevant studies by our research group, see:
33. d) Z. Jiang, Z. Liang, X. Wu, Y. Lu, Chem. Commun. 2006, 2801;
34. e) X. Wu, Z. Jiang, H.-M. Shen, Y. Lu, Adv. Synth. Catal. 2007,349, 812;
35. f) L. Cheng, X. Wu, Y. Lu, Org. Biomol. Chem. 2007, 5, 1018;
36. g) L. Cheng, X. Han, H. Huang, M. W. Wong, Y. Lu, Chem. Commun. 2007, 4143.
37. For recent reviews on the synthesis of fluorinated molecules, see : a) K. Mikami, Y. Itoh, M. Yamanaka, Chem. Rev. 2004, 104, 1;
38. b) V. A. Brunet, D. O'Hagan, Angew. Chem. 2008, 120, 1198;
39. Angew. Chem. Int. Ed. 2008, 47, 1179;
40. c) G. K. S. Prakash, P. Beier, Angew. Chem. 2006, 118, 2228;
41. Angew. Chem. Int. Ed. 2006, 45, 2172;
42. d) P. M. Pihko, Angew. Chem. 2006, 118, 558;
43. Angew. Chem. Int. Ed. 2006, 45, 544;
44. e) M. Oestreich, Angew. Chem. 2005, 117, 2376;
45. Angew. Chem. Int. Ed. 2005, 44, 2324;
46. f) H. Ibrahim, A. Togni, Chem. Commun. 2004, 1147;
47. g) R. Smits, C. D. Cadicamo, K. Burger, B. Koksch, Chem. Soc. Rev. 2008, 37, 1727.
48. For selected examples, see: a) L. Hintermann, A. Togni, Angew. Chem. 2000, 112, 4530;
49. Angew. Chem. Int. Ed. 2000, 39, 4359;
50. b) Y. Hamashima, K. Yagi, H. Takano, L. Tamas, M. Sodeoka, J. Am. Chem. Soc. 2002,124, 14530;
51. c) Y. Hamashima, T. Suzuki, H. Takano, Y. Shimura, M. Sodeoka, J. Am. Chem. Soc. 2005, 127,10164;
52. d) H. R. Kim, D. Y. Kim, Tetrahedron Lett. 2005, 46, 3115;
53. e) J.-A. Ma, D. Cahard, Tetrahedron: Asymmetry 2004, 15, 1007;
54. f) N. Shibata, J. Kohno, K. Takai, T. Ishimaru, S. Nakamura, T. Tom, S. Kanemasa, Angew. Chem. 2005, 117, 4276;
55. Angew. Chem. Int. Ed. 2005, 44, 4204;
56. g) D. S. Reddy, N. Shibata, J. Nagai, S. Nakamura, T. Toru, S. Kanemasa, Angew. Chem. 2008,120,110;
57. Angew. Chem. Int. Ed. 2008,47,164;
58. h) M. Nakamura, A. Hajra, K. Endo, E. Nakamura, Angew. Chem. 2005,117, 7414;
59. Angew. Chem. Int. Ed. 2005, 44, 7248;
60. i) E. C. Burger, B. R. Barron, J. A. Tunge, Synlett 2007, 2824.
61. a) D. Y Kim, E. J. Park, Org. Lett. 2002,4, 545;
62. b) S. Brandes, B. Niess, M. Bella, A. Prieto, J. Overgaard, K. A. Jørgensen, Chem. Eur. J. 2006, 12, 6039;
63. c) T. Ishimaru, N. Shibata, T. Horikawa, N. Yasuda, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. 2008, 120, 4225;
64. Angew. Chem. Int. Ed. 2008, 47, 4157.
65. a) X. Han, J. Luo, C. Liu, Y. Lu, Chem. Commun. 2009, 2044;
66. b) C. Ding, K. Mauroka, Synlett 2009,664;
67. c) Z. Jiang, Y. Pan, Y. Zhao, T. Ma, R. Lee, Y. Yang, K.-W. Huang, M. W. Wong, C.-H. Tan, Angew. Chem. 2009,121,3681;
68. Angew. Chem. Int. Ed. 2009, 48, 3627;
69. d) G. K. S. Prakash, F. Wang, T. Stewart, T. Mathew, G. A. Olah, Proc. Natl. Acad. Sci. USA 2009,106, 4090.
70. a) S. Lou, B. M. Taoka, A. Ting, S. E. Schaus, J. Am. Chem. Soc. 2005,127, 11256;
71. b) J. Song, Y. Wang, L. Deng, J. Am. Chem. Soc. 2006,128, 6048;
72. c) A. L. Tillman, J. Ye, D. J. Dixon, Chem. Commun. 2006, 1191.
73. Imines other than the N-Boc imine were also examined under the same conditions at room temperature: the use of the corresponding N-benzylimine led to the formation of only a trace amount of the product, the N-p- methoxyphenylimine and the N-p-nitrobenzenesulfonylimine gave the products in less than 20 % yield, and the N-benzyloxycarbonylimine afforded the Mannich products in quantitative yield with d.r. 4:1 and 75 % ee.
74. J Luo, L.-W Xu, R. A. S. Hay, Y. Lu, Org. Lett. 2009, 11, 437.
75. See the Supporting Information for details.
76. For the antibacterial activity and synthesis of ß-lactams, see: a) J. D. Buynak, Curr. Med. Chem. 2004, 11, 1951;
77. b) A. Brandi, S. Cicchi, F. C. Cordero, Chem. Rev. 2008, 108, 3988;
78. c) R. Pal, S. C. Ghosh, K. Chandra, A. Basak, Synlett 2007, 2321.
79. CCDC 745901 (8) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data-request/cif.