Organocatalytic asymmetric conjugate addition of aldehydes to nitroolefins: Identification of catalytic intermediates and the stereoselectivity-determining step by ESI-MS

Angewandte Chemie - International Edition

Volumn 52, Issue 48, 2013, Pages 12619-12623

  Bächle, Florian ^a   Duschmalé, Jörg ^b   Ebner, Christian ^a   Pfaltz, Andreas ^a   Wennemers, Helma ^b  

^a UNIVERSITY OF BASEL   (Switzerland)

^b ETH ZURICH   (Switzerland)

Author keywords

asymmetric catalysis; mass spectrometry; organocatalysis; peptides; reaction mechanisms

Indexed keywords

1 ,4-ADDITION; ASYMMETRIC CATALYSIS; ASYMMETRIC CONJUGATE ADDITION; BACK REACTION; CATALYTIC INTERMEDIATES; ORGANOCATALYSIS; ORGANOCATALYTIC; REACTION MECHANISM;

ALDEHYDES; CATALYSIS; MASS SPECTROMETRY; PEPTIDES; REACTION KINETICS;

ENANTIOSELECTIVITY;

EID: 84887970028     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201305338     Document Type: Article

References (81)

1. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569.
2. Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621.
3. C. T. Wong, Tetrahedron Lett. 2009, 50, 811-813
4. D. A. Yalalov, S. B. Tsogoeva, T. E. Shubina, I. M. Martynova, T. Clark, Angew. Chem. 2008, 120, 6726-6730
5. Angew. Chem. Int. Ed. 2008, 47, 6624-6628
6. C. T. Wong, Tetrahedron 2009, 65, 7491-7497
7. S. Belot, A. Quintard, N. Krause, A. Alexakis, Adv. Synth. Catal. 2010, 352, 667-695
8. C. T. Wong, Tetrahedron 2012, 68, 481-487.
9. For a review see:, M. Klussmann, in Science of Synthesis: Asymmetric Organocatalysis, Vol. 2 (Eds.:, B. List, K. Maruoka,), Thieme, Stuttgart, 2012, pp. 633-671. For selected examples see
10. B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 5839-5842
11. D. Seebach, A. K. Beck, D. M. Badine, M. Limbach, A. Eschenmoser, A. M. Treasurywala, R. Hobi, W. Prikoszovich, B. Linder, Helv. Chim. Acta 2007, 90, 425-471
12. N. Zotova, L. J. Broadbelt, A. Armstrong, D. G. Blackmond, Bioorg. Med. Chem. Lett. 2009, 19, 3934-3937
13. M. B. Schmid, K. Zeitler, R. M. Gschwind, Angew. Chem. 2010, 122, 5117-5123
14. Angew. Chem. Int. Ed. 2010, 49, 4997-5003
15. M. B. Schmid, K. Zeitler, R. M. Gschwind, J. Am. Chem. Soc. 2011, 133, 7065-7074.
16. C. Marquez, J. O. Metzger, Chem. Commun. 2006, 1539-1541
17. C. A. Marquez, F. Fabbretti, J. O. Metzger, Angew. Chem. 2007, 119, 7040-7042
18. Angew. Chem. Int. Ed. 2007, 46, 6915-6917.
19. J. Vicario, Organocatalytic Enantioselective Conjugate Addition Reactions, Royal Society of Chemistry, Cambridge, 2010.
20. J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740
21. A. Alexakis, O. Andrey, Org. Lett. 2002, 4, 3611-3614
22. D. Enders, A. Seki, Synlett 2002, 26-28
23. H. J. Martin, B. List, Synlett 2003, 1901-1902
24. N. Mase, R. Thayumanavan, F. Tanaka, C. F. Barbas III, Org. Lett. 2004, 6, 2527-2530
25. O. Andrey, A. Alexakis, A. Tomassini, G. Bernardinelli, Adv. Synth. Catal. 2004, 346, 1147-1168
26. M. P. Lalonde, Y. Chen, E. N. Jacobsen, Angew. Chem. 2006, 118, 6514-6518
27. Angew. Chem. Int. Ed. 2006, 45, 6366-6370
28. C. Palomo, S. Vera, A. Mielgo, E. Gomez-Bengoa, Angew. Chem. 2006, 118, 6130-6133
29. Angew. Chem. Int. Ed. 2006, 45, 5984-5987
30. J. Wang, H. Li, B. Lou, L. Zu, H. Guo, W. Wang, Chem. Eur. J. 2006, 12, 4321-4332
31. H. Uehara, C. F. Barbas III, Angew. Chem. 2009, 121, 10032-10036
32. Angew. Chem. Int. Ed. 2009, 48, 9848-9852.
33. J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjrsgaard, K. A. Jorgensen, J. Am. Chem. Soc. 2005, 127, 18296-18304
34. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284-4287
35. Angew. Chem. Int. Ed. 2005, 44, 4212-4215
36. Y. Hayashi, T. Itoh, M. Ohkubo, H. Ishikawa, Angew. Chem. 2008, 120, 4800-4802
37. Angew. Chem. Int. Ed. 2008, 47, 4722-4724
38. Y. Chi, L. Guo, N. A. Kopf, S. H. Gellman, J. Am. Chem. Soc. 2008, 130, 5608-5609
39. S. Zhu, S. Yu, D. Ma, Angew. Chem. 2008, 120, 555-558
40. Angew. Chem. Int. Ed. 2008, 47, 545-548
41. P. García-García, A. Ladepeche, R. Halder, B. List, Angew. Chem. 2008, 120, 4797-4799
42. Angew. Chem. Int. Ed. 2008, 47, 4719-4721
43. H. Ishikawa, T. Suzuki, Y. Hayashi, Angew. Chem. 2009, 121, 1330-1333
44. Angew. Chem. Int. Ed. 2009, 48, 1304-1307
45. D. Enders, C. Wang, A. Greb, Adv. Synth. Catal. 2010, 352, 987-992
46. H. Rahaman, A. Madarasz, I. Papai, P. M. Pihko, Angew. Chem. 2011, 123, 6247-6251
47. Angew. Chem. Int. Ed. 2011, 50, 6123-6127.
48. M. Wiesner, J. D. Revell, H. Wennemers, Angew. Chem. 2008, 120, 1897-1900
49. Angew. Chem. Int. Ed. 2008, 47, 1871-1874
50. M. Wiesner, J. D. Revell, S. Tonazzi, H. Wennemers, J. Am. Chem. Soc. 2008, 130, 5610-5611
51. M. Wiesner, M. Neuburger, H. Wennemers, Chem. Eur. J. 2009, 15, 10103-10109
52. M. Wiesner, H. Wennemers, Synthesis 2010, 1568-1571
53. Y. Arakawa, M. Wiesner, H. Wennemers, Adv. Synth. Catal. 2011, 353, 1201-1206
54. Y. Arakawa, H. Wennemers, ChemSusChem 2013, 6, 242-245.
55. M. Wiesner, G. Upert, G. Angelici, H. Wennemers, J. Am. Chem. Soc. 2010, 132, 6-7
56. J. Duschmalé, J. Wiest, M. Wiesner, H. Wennemers, Chem. Sci. 2013, 4, 1312-1318.
57. J. Duschmalé, H. Wennemers, Chem. Eur. J. 2012, 18, 1111-1120
58. R. Kastl, H. Wennemers, Angew. Chem. 2013, 125, 7369-7373
59. Angew. Chem. Int. Ed. 2013, 52, 7228-7232.
60. C. Markert, A. Pfaltz, Angew. Chem. 2004, 116, 2552-2554
61. C. Markert, P. Rösel, A. Pfaltz, J. Am. Chem. Soc. 2008, 130, 3234-3235
62. C. A. Müller, A. Pfaltz, Angew. Chem. 2008, 120, 3411-3414
63. Angew. Chem. Int. Ed. 2008, 47, 3363-3366
64. C. Ebner, C. A. Müller, C. Markert, A. Pfaltz, J. Am. Chem. Soc. 2011, 133, 4710-4713
65. C. A. Müller, C. Markert, A. M. Teichert, A. Pfaltz, Chem. Commun. 2009, 1607-1618
66. A. Teichert, A. Pfaltz, Angew. Chem. 2008, 120, 3408-3410
67. Angew. Chem. Int. Ed. 2008, 47, 3360-3362
68. I. Fleischer, A. Pfaltz, Chem. Eur. J. 2010, 16, 95-99.
69. L. S. Santos, Reactive Intermediates, Wiley-VCH, Weinheim, 2010
70. W. Zhu, Y. Yuan, P. Zhou, L. Zeng, H. Wang, L. Tang, B. Guo, B. Chen, Molecules 2012, 17, 11507-11537
71. S. B. Tsogoeva, S. Wei, Chem. Commun. 2006, 1451-1453
72. O. V. Maltsev, A. O. Chizhov, S. G. Zlotin, Chem. Eur. J. 2011, 17, 6109-6117
73. M. W. Alachraf, P. P. Handayani, M. R. Huttl, C. Grondal, D. Enders, W. Schrader, Org. Biomol. Chem. 2011, 9, 1047-1053.
74. G. Stork, A. Brizzola, H. Landesman, J. Szmuszkovicz, R. Terrell, J. Am. Chem. Soc. 1963, 85, 207-222.
75. K. Patora-Komisarska, M. Benohoud, H. Ishikawa, D. Seebach, Y. Hayashi, Helv. Chim. Acta 2011, 94, 719-745
76. J. Burés, A. Armstrong, D. G. Blackmond, J. Am. Chem. Soc. 2011, 133, 8822-8825
77. D. Seebach, X. Sun, C. Sparr, M.-O. Ebert, W. B. Schweizer, A. K. Beck, Helv. Chim. Acta 2012, 95, 1064-1078
78. G. Sahoo, H. Rahaman, Á. Madarász, I. Pápai, M. Melarto, A. Valkonen, P. M. Pihko, Angew. Chem. 2012, 124, 13321-13325
79. Angew. Chem. Int. Ed. 2012, 51, 13144-13148
80. D. Seebach, X. Sun, M.-O. Ebert, W. B. Schweizer, N. Purkayastha, A. K. Beck, J. Duschmalé, H. Wennemers, T. Mukaiyama, M. Benohoud, Y. Hayashi, M. Reiher, Helv. Chim. Acta, 2013, 96, 799-852.
81. J. Bures, A. Armstrong, D. G. Blackmond, J. Am. Chem. Soc. 2012, 134, 6741-6750.