Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis

Angewandte Chemie - International Edition

Volumn 52, Issue 47, 2013, Pages 12354-12358

  Jin, Zhichao ^a   Xu, Jianfeng ^a   Yang, Song ^b   Song, Bao An ^b   Chi, Yonggui Robin ^a  

^a Nanyang Technological University   (Singapore)

^b GUIZHOU UNIVERSITY   (China)

Author keywords

, unsaturated ketones; enantioselective sulfonation; Michael addition; N S bond cleavage; organocatalysis

Indexed keywords

BOND CLEAVAGES; ENANTIOSELECTIVE; MICHAEL ADDITIONS; ORGANOCATALYSIS; UNSATURATED KETONES;

ADDITION REACTIONS; CATALYSTS; ENANTIOSELECTIVITY; HYDROGEN BONDS; KETONES; NITROGEN COMPOUNDS; REACTION KINETICS; SULFONATION;

ORGANIC COMPOUNDS;

AMINE; CARBENE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; IMINE; KETONE; METHANE; SULFONE; THIOUREA;

ARTICLE; CATALYSIS; CHEMISTRY; ENANTIOSELECTIVE SULFONATION; MICHAEL ADDITION; N S BOND CLEAVAGE; ORGANOCATALYSIS; STEREOISOMERISM; Α,Β-UNSATURATED KETONES;

ENANTIOSELECTIVE SULFONATION; MICHAEL ADDITION; N S BOND CLEAVAGE; ORGANOCATALYSIS; Α,Β-UNSATURATED KETONES;

AMINES; CATALYSIS; HETEROCYCLIC COMPOUNDS; IMINES; KETONES; METHANE; STEREOISOMERISM; SULFONES; THIOUREA;

EID: 84887538326     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201305023     Document Type: Article

References (86)

1. B. M. Trost, Acc. Chem. Res. 1978, 11, 453
2. P. Vogel, M. Turks, L. Bouchez, D. Markovic̈, A. Varela- Álvarez, J. Á. Sordo, Acc. Chem. Res. 2007, 40, 931.
3. W. M. J. Wolf, Mol. Struct. 1999, 474, 113
4. S. Trivedi, P. C. Patidar, P. K. Chaurasiya, Pharma Chem. 2010, 2, 369.
5. R. W. Murray, R. Jeyararnan, M. K. Pilley, J. Org. Chem. 1987, 52, 746.
6. J. J. Burger, T. B. R. A. Chen, E. R. DeWaard, H. O. Huisman, Tetrahedron 1980, 36, 723.
7. H. Fukuda, F. J. Frank, W. E. Truce, J. Org. Chem. 1963, 28, 1420.
8. K. Hiroi, K. Makino, Chem. Lett. 1986, 617
9. B. M. Trost, M. G. Organ, G. A. O'Doherty, J. Am. Chem. Soc. 1995, 117, 9662
10. H.-J. Gais, T. Jagusch, N. Spalthoff, F. Gerhards, M. Frank, G. Raabe, Chem. Eur. J. 2003, 9, 4202
11. M. Ueda, J. F. Hartwig, Org. Lett. 2010, 12, 92; for a related study, see
12. X.-S. Wu, Y. Chen, M.-B. Li, M.-G. Zhou, S.-K. Tian, J. Am. Chem. Soc. 2012, 134, 14694.
13. For selected reviews on NHC catalysis, see
14. D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606
15. N. Marion, S. Díez-González, S. P. Nolan, Angew. Chem. 2007, 119, 3046
16. Angew. Chem. Int. Ed. 2007, 46, 2988
17. A. J. Arduengo, L. I. Iconaru, Dalton Trans. 2009, 6903
18. J. L. Moore, T. Rovis, Top. Curr. Chem. 2011, 291, 77
19. A. T. Biju, N. Kuhl, F. Glorius, Acc. Chem. Res. 2011, 44, 1182
20. P.-C. Chiang, J. W. Bode, TCI MAIL 2011, 149, 2
21. V. Nair, R. S. Menon, A. T. Biju, C. R. Sinu, R. R. Paul, A. Jose, V. Sreekumar, Chem. Soc. Rev. 2011, 40, 5336
22. A. Grossmann, D. Enders, Angew. Chem. 2012, 124, 320
23. Angew. Chem. Int. Ed. 2012, 51, 314
24. D. T. Cohen, K. A. Scheidt, Chem. Sci. 2012, 3, 53
25. X. Bugaut, F. Glorius, Chem. Soc. Rev. 2012, 41, 3511.
26. S. P. Lathrop, T. Rovis, J. Am. Chem. Soc. 2009, 131, 13628
27. B.-C. Hong, N. S. Dange, C.-S. Hsu, J.-H. Liao, Org. Lett. 2010, 12, 4812
28. H. Jiang, B. Gschwend, Ł. Albrecht, K. A. Jørgensen, Org. Lett. 2010, 12, 5052
29. D. Enders, A. Grossmann, H. Huang, G. Raabe, Eur. J. Org. Chem. 2011, 4298
30. B.-C. Hong, N. S. Dange, C.-S. Hsu, J.-H. Liao, G.-H. Lee, Org. Lett. 2011, 13, 1338
31. Y.-Z. Liu, J. Zhang, P.-F. Xu, Y.-C. Luo, J. Org. Chem. 2011, 76, 7551
32. C. B. Jacobsen, K. L. Jensen, J. Udmark, K. A. Jørgensen, Org. Lett. 2011, 13, 4790
33. C. B. Jacobsen, L. Albrecht, J. Udmark, K. A. Jørgensen, Org. Lett. 2012, 14, 5526
34. C. Ma, Z.-J. Jia, X.-J. Liu, Q.-Q. Zhou, L. Dong, Y.-C. Chen, Angew. Chem. 2013, 125, 982
35. Angew. Chem. Int. Ed. 2013, 52, 948.
36. S. Simonovic, J.-C. Frison, H. Koyuncu, A. C. Whitwood, R. E. Douthwaite, Org. Lett. 2009, 11, 245; for examples of other NHC-catalyzed reactions involving imines, see
37. M. He, J. W. Bode, Org. Lett. 2005, 7, 3131
38. G.-Q. Li, L.-X. Dai, S.-L. You, Chem. Commun. 2007, 852
39. A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 5334
40. L, He, Y.-R. Zhang, X.-L. Huang, S. Ye, Synthesis 2008, 2825
41. N. Duguet, A. Donaldson, S. M. Leckie, J. Douglas, P. Shapland, T. B. Brown, G. Churchill, A. M. Z. Slawin, A. D. Smith, Tetrahedron: Asymmetry 2010, 21, 582
42. R. De Vreese, M. D'Hooghe, Beilstein J. Org. Chem. 2012, 8, 398.
43. D.-D. Chen, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2008, 73, 5578.
44. M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901; for selected examples, see
45. T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672
46. Y. Sohtome, A. Tanatani, Y. Hashimoto, K. Nagasawa, Tetrahedron Lett. 2004, 45, 5589
47. R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem. 2005, 117, 6734
48. Angew. Chem. Int. Ed. 2005, 44, 6576
49. J. Wang, H. Li, X. Yu, L. Zu, W. Wang, Org. Lett. 2005, 7, 4293
50. S. B. Tsogoeva, S. Wei, Chem. Commun. 2006, 1451
51. T. Marcelli, R. N. S. van der Haas, J. H. van Maarseveen, H. Hiemstra, Angew. Chem. 2006, 118, 943
52. Angew. Chem. Int. Ed. 2006, 45, 929; for selected reviews, see
53. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713
54. S. J. Connon, Chem. Commun. 2008, 2499; for recent reviews on ion-pair interactions, see
55. M. Mahlau, B. List, Angew. Chem. 2013, 125, 540
56. Angew. Chem. Int. Ed. 2013, 52, 518
57. K. Brak, E. N. Jacobsen, Angew. Chem. 2013, 125, 558
58. Angew. Chem. Int. Ed. 2013, 52, 534.
59. L. He, T.-Y. Jian, S. Ye, J. Org. Chem. 2007, 72, 7466
60. A. D. DiRocco, K. M. Oberg, T. Rovis, J. Am. Chem. Soc. 2012, 134, 6143; for the deprotonation of alcohols by NHCs, see
61. S. D. Sarkar, S. Grimme, A. Studer, J. Am. Chem. Soc. 2010, 132, 1190.
62. T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592
63. Angew. Chem. Int. Ed. 2004, 43, 1566
64. D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356
65. G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005, 127, 15696
66. D. Nakashima, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 9626
67. G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496
68. I. Čoric̈, B. List, Nature 2012, 483, 315
69. Z. Chen, B. Wang, Z. Wang, G. Zhu, J. Sun, Angew. Chem. 2013, 125, 2081
70. Angew. Chem. Int. Ed. 2013, 52, 2027; for reviews, see
71. M. Rueping, B. J. Nachtsheim, W. Ieawsuwan, I. Atodiresei, Angew. Chem. 2011, 123, 6838
72. Angew. Chem. Int. Ed. 2011, 50, 6706
73. L. Ren, T. Lei, L.-Z. Gong, Chem. Commun. 2011, 47, 11683
74. C. Zheng, S.-L. You, Chem. Soc. Rev. 2012, 41, 2498.
75. A. Kumar, M. K. Muthyala, Tetrahedron Lett. 2011, 52, 5368.
76. V. Nair, S. Vellalath, M. Poonoth, E. Suresh, J. Am. Chem. Soc. 2006, 128, 8736
77. P.-C. Chiang, J. Kaeobamrung, J. W. Bode, J. Am. Chem. Soc. 2007, 129, 3520
78. B. Cardinal-David, D. E. A. Raup, K. A. Scheidt, J. Am. Chem. Soc. 2010, 132, 5345
79. X. Zhao, K. E. Ruhl, T. Rovis, Angew. Chem. 2012, 124, 12496
80. Angew. Chem. Int. Ed. 2012, 51, 12330
81. J. Mo, R. Yang, X. Chen, B. Tiwari, Y. R. Chi, Org. Lett. 2013, 15, 50.
82. B. Sreedhar, M. A. Reddy, P. S. Reddy, Synlett 2008, 1949
83. A. A. Sayed, M. S. Wadia, J. Chem. Res. Synop. 2001, 362.
84. J. Skarżewski, R. Siedlecka, E. Wojaczyńska, M. Zielińska-Błajet, Tetrahedron: Asymmetry 2002, 13, 2105.
85. C. J. Thibodeaux, W. Chang, H. Liu, Chem. Rev. 2012, 112, 1681
86. A. K. Kumar, Int. J. Pharm. Pharm. Sci. 2013, 5, 467.