Catalytic asymmetric α-aldol reaction of vinylogous N-heterocyclic carbene enolates: Formation of quaternary and labile tertiary stereocenters

Organic Letters

Volumn 16, Issue 9, 2014, Pages 2450-2453

  Dong, Xiuqin ^a   Sun, Jianwei ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84899887814     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500830a     Document Type: Article

References (96)

1. Ojima, I. Catalytic Asymmetric Synthesis, 3 rd ed.; John Wiley: Hoboken, NJ; 2010.
2. Christmann, M. and Bräse, S. Asymmetric Synthesis II: More Methods and Applications; Wiley-VCH: Hoboken, NJ, 2012.
3. Enders, D.; Narine, A. A. J. Org. Chem. 2008, 73, 7857
4. Scheffler, U.; Mahrwald, R. Chem.-Eur. J. 2013, 19, 14346
5. Mahrwald, R. Drug Discovery Today: Technologies 2013, 10, e29
6. Volla, C. M. R.; Atodiresei, I.; Rueping, M. Chem. Rev. 2014, 114, 2390
7. Moore, J. L.; Rovis, T. Top. Curr. Chem. 2011, 291, 77
8. Vora, H. U.; Rovis, T. Aldrichimica Acta 2011, 44, 3
9. Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011, 40, 5336
10. Rong, Z.-Q.; Zhang, W.; Yang, G.-Q.; You, S.-L. Curr. Org. Chem. 2011, 15, 3077
11. Biju, A. T.; Kuhl, N.; Glorius, F. Acc. Chem. Res. 2011, 44, 1182
12. Chiang, P.-C.; Bode, J. W. TCI MAIL 2011, 149, 2
13. Vora, H. U.; Wheeler, P.; Rovis, T. Adv. Synth. Catal. 2012, 354, 1617
14. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511
15. Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 11686
16. Cohen, D. T.; Scheidt, K. A. Chem. Sci. 2012, 3, 53
17. Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314
18. Bode, J. W. Nat. Chem. 2013, 5, 813
19. Sarkar, S. D.; Biswas, A.; Samanta, R. C.; Studer, A. Chem.-Eur. J. 2013, 19, 4664
20. Ryan, S. J.; Candish, L.; Lupton, D. W. Chem. Soc. Rev. 2013, 42, 4906
21. Chauhan, P.; Ender, D. Angew. Chem., Int. Ed. 2014, 53, 1485
22. Mahatthananchai, J.; Bode, J. W. Acc. Chem. Res. 2014, 47, 696
23. Douglas, J.; Churchill, G.; Smith, A. D. Synthesis 2012, 44, 2295
24. Chen, X.-Y.; Ye, S. Synlett 2013, 24, 1614
25. Maji, B.; Mayr, H. Angew. Chem., Int. Ed. 2013, 52, 11163
26. Reynolds, N. T.; De Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518
27. Reynolds, N. T.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 16406
28. He, M.; Struble, J. R.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 8418
29. He, M.; Uc, G. J.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 15088
30. He, M.; Beahm, B. J.; Bode, J. W. Org. Lett. 2008, 10, 3817
31. Zhang, Y.-R.; He, L.; Wu, X.; Shao, P.-L.; Ye, S. Org. Lett. 2008, 10, 277
32. Duguet, N.; Campbell, C. D.; Slawin, A. M. Z.; Smith, A. D. Org. Biomol. Chem. 2008, 6, 1108
33. Zhang, Y. R.; Lv, H.; Zhou, D.; Ye, S. Chem.-Eur. J. 2008, 14, 8473
34. Wang, X.-N.; Shao, P.-L.; Lv, H.; Ye, S. Org. Lett. 2009, 11, 4029
35. Lv, H.; Chen, X.-Y.; Sun, L.-H.; Ye, S. J. Org. Chem. 2010, 75, 6973
36. Kaeobamrung, J.; Kozlowski, M. C.; Bode, J. W. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20661
37. Jian, T.-Y.; Shao, P.-L.; Ye, S. Chem. Commun. 2011, 47, 2381
38. Wang, X.-N.; Shen, L.-T.; Ye, S. Org. Lett. 2011, 13, 6382
39. Rong, Z.-Q.; Jia, M.-Q.; You, S.-L. Tetrahedron 2011, 67, 9329
40. Fang, X.; Chen, X.; Chi, Y. R. Org. Lett. 2011, 13, 4708
41. Lv, H.; Mo, J.; Fang, X.; Chi, Y. R. Org. Lett. 2011, 13, 5366
42. Hao, L.; Du, Y.; Lv, H.; Chen, X.; Jiang, H.; Shao, Y.; Chi, Y. R. Org. Lett. 2012, 14, 2154
43. Yang, L.; Wang, F.; Chua, P. J.; Lv, Y.; Zhong, L.-J.; Zhong, G. Org. Lett. 2012, 14, 2894
44. Zhao, X.; Ruhl, K. E.; Rovis, T. Angew. Chem., Int. Ed. 2012, 51, 12330
45. Fu, Z.; Sun, H.; Chen, S.; Tiwari, B.; Li, G.; Chi, Y. R. Chem. Commun. 2013, 49, 261
46. Leckie, S. M.; Brown, T. B.; Pryde, D.; Lebl, T.; Slawin, A. M. Z.; Smith, A. D. Org. Biomol. Chem. 2013, 11, 3230
47. Davies, A. T.; Taylor, J. E.; Douglas, J.; Collett, C. J.; Morrill, L. C.; Fallan, C.; Slawin, A. M. Z.; Churchill, G.; Smith, A. D. J. Org. Chem. 2013, 78, 9243
48. Douglas, J.; Taylor, J. E.; Churchill, G.; Slawin, A. M. Z.; Smith, A. D. J. Org. Chem. 2013, 78, 3925
49. McCusker, E. O.; Scheidt, K. A. Angew. Chem., Int. Ed. 2013, 52, 13616
50. Ni, Q.; Zhang, H.; Grossmann, A.; Loh, C. C. J.; Merkens, C.; Enders, D. Angew. Chem., Int. Ed. 2013, 52, 13562
51. Chiang, P.-C.; Kaeobamrung, J.; Bode, J. W. J. Am. Chem. Soc. 2007, 129, 3520
52. Wadamoto, M.; Phillips, E. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 10098
53. Phillips, E. M.; Wadamoto, M.; Chan, A.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 3107
54. He, M.; Bode, J. W. J. Am. Chem. Soc. 2008, 130, 418
55. Li, Y.; Wang, X.-Q.; Zheng, C.; You, S.-L. Chem. Commun. 2009, 5823
56. Cardinal-David, B.; Raup, D. E. A.; Scheidt, K. A. J. Am. Chem. Soc. 2010, 132, 5345
57. Cohen, D. T.; Cardinal-David, B.; Scheidt, K. A. Angew. Chem., Int. Ed. 2011, 50, 1678
58. Fang, X.; Jiang, K.; Xing, C.; Hao, L.; Chi, Y. R. Angew. Chem., Int. Ed. 2011, 50, 1910
59. Biswas, A.; De Sarkar, S.; Tebben, L.; Studer, A. Chem. Commun. 2012, 48, 5190
60. Cohen, D. T.; Eichman, C. C.; Phillips, E. M.; Zarefsky, E. R.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 7309
61. Fu, Z.; Xu, J.; Zhu, T.; Leong, W. W. Y.; Chi, Y. R. Nat. Chem. 2013, 5, 835
62. Wang, X.-N.; Lv, H.; Huang, X.-L.; Ye, S. Org. Biomol. Chem. 2009, 7, 346
63. Vora, H. U.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 2860
64. Concellón, C.; Duguet, N.; Smith, A. D. Adv. Synth. Catal. 2009, 351, 3001
65. Huang, X.-L.; He, L.; Shao, P.-L.; Ye, S. Angew. Chem., Int. Ed. 2009, 48, 192
66. Douglas, J.; K. Ling, B.; Concellón, C.; Churchill, G.; Slawin, A. M. Z.; Smith, A. D. Eur. J. Org. Chem. 2010, 5863
67. Shao, P.-L.; Chen, X.-Y.; Ye, S. Angew. Chem., Int. Ed. 2010, 49, 8412
68. Jian, T.-Y.; He, L.; Tang, C.; Ye, S. Angew. Chem., Int. Ed. 2011, 50, 9104
69. Taylor, J. E.; Daniels, D. S. B.; Smith, A. D. Org. Lett. 2013, 15, 6058
70. It is presumably because of the favorable thermodynamics in the ring-closing step to facilitate catalyst turnover. A concerted pathway for a [4 + 2] example was proposed based on calculations: Allen, S. E.; Mahhatthananchai, J.; Bode, J. W.; Kozlowski, M. C. J. Am. Chem. Soc. 2012, 134, 12098
71. For an example, which generates β- instead of α-chirality, see: Kawanaka, Y.; Phillips, E. M.; Scheidt, K. A. J. Am. Chem. Soc. 2009, 131, 18028
72. Shen, L.-T.; Shao, P.-L.; Ye, S. Adv. Synth. Catal. 2011, 353, 1943
73. Mo, J.; Chen, X.; Chi, Y. R. J. Am. Chem. Soc. 2012, 134, 8810
74. Chen, X.; Yang, S.; Song, B.-A.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 11134
75. Xu, J.; Jin, Z.; Chi, Y. R. Org. Lett. 2013, 15, 5028
76. Wang, M.; Huang, Z.; Xu, J.; Chi, Y. R. J. Am. Chem. Soc. 2014, 136, 1214
77. Zhao, Y.-M.; Cheung, M. S.; Lin, Z.; Sun, J. Angew. Chem., Int. Ed. 2012, 51, 10359
78. Chen, X.-Y.; Xia, F.; Cheng, J.-T.; Ye, S. Angew. Chem., Int. Ed. 2013, 52, 10644
79. Casiraghi, G.; Zanardi, F. Chem. Rev. 2000, 100, 1929
80. Denmark, S. E.; Heemstra, J. R.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682
81. Xu, B.; Hammond, G. B. Synlett 2010, 1442
82. Casiraghi, G.; Battistini, L.; Curti, C.; Rassu, G.; Zanardi, F. Chem. Rev. 2011, 111, 3076
83. Zhao, Y.-M.; Tam, Y.; Wang, Y.-J.; Li, Z.; Sun, J. Org. Lett. 2012, 14, 1398
84. Dong, X.; Zhao, Y.-M.; Sun, J. Synlett 2013, 24, 1221
85. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
86. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
87. Jeschke, P. ChemBioChem 2004, 5, 570
88. Hung, M. H.; Farnham, W. B.; Feiring, A. E.; Rozen, S. In Fluoropolymers: Synthesis; Hougham, G.; Cassidy, P. E.; Johns, K.; Davidson, T., Eds.; Kluwer Academic/Plenum Publishers: New York, 1999; Vol. 1, p 51.
89. Davies, H. W.; Jin, Q. J. Am. Chem. Soc. 2004, 126, 10862
90. Lou, S.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 5010
91. Skucas, E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2012, 134, 9090
92. Precatalyst B was first disclosed by Bode and co-workers. See ref 6a and: Struble, J. R.; Bode, J. W.; Lian, Y.; Davies, H. M. L. Org. Synth. 2010, 87, 362
93. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p 696.
94. Frezza, M.; Balestrino, D.; Soulere, L.; Reverchon, S.; Queneau, Y.; Forestier, C.; Doutheau, A. Eur. J. Org. Chem. 2006, 4731
95. Hall, A.; Farthing, C. N.; Castro Pineiro, J. L. Patent WO 098213A1, 2012.
96. Alvaro, G.; Décor, A.; Hamprecht, D.; Marasco, A. Patent WO 168710A1, 2012.