N-heterocyclic carbene catalyzed formal [3+2] annulation reaction of enals: An efficient enantioselective access to spiro-heterocycles

Angewandte Chemie - International Edition

Volumn 53, Issue 38, 2014, Pages 10232-10236

  Guo, Chang ^a   Schedler, Michael ^a   Daniliuc, Constantin G ^a   Glorius, Frank ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

asymmetric synthesis; enals; N heterocyclic carbenes; organocatalysis; spiro heterocycles

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS; ENALS; HETEROCYCLES; N-HETEROCYCLIC CARBENES; ORGANOCATALYSIS;

ORGANIC COMPOUNDS;

EID: 84911158909     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201405381     Document Type: Article

References (100)

1. D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606
2. N. Marion, S. Díez-González, S. P. Nolan, Angew. Chem. 2007, 119, 3046
3. Angew. Chem. Int. Ed. 2007, 46, 2988
4. V. Nair, S. Vellalath, B. P. Babu, Chem. Soc. Rev. 2008, 37, 2691
5. E. M. Phillips, A. Chan, K. A. Scheidt, Aldrichimica Acta 2009, 42, 55
6. J. L. Moore, T. Rovis, Top. Curr. Chem. 2010, 291, 77
7. A. T. Biju, N. Kuhl, F. Glorius, Acc. Chem. Res. 2011, 44, 1182
8. H. U. Vora, T. Rovis, Aldrichimica Acta 2011, 44, 3
9. V. Nair, R. S. Menon, A. T. Biju, C. R. Sinu, R. R. Paul, A. Jose, V. Sreekumar, Chem. Soc. Rev. 2011, 40, 5336
10. H. U. Vora, T. Rovis, Aldrichimica Acta 2011, 44, 3
11. P.-C. Chiang, J. W. Bode, TCI Mail 2011, 149, 2
12. K. Hirano, I. Piel, F. Glorius, Chem. Lett. 2011, 40, 786
13. J. Izquierdo, G. E. Hutson, D. T. Cohen, K. A. Scheidt, Angew. Chem. 2012, 124, 11854
14. Angew. Chem. Int. Ed. 2012, 51, 11686
15. D. T. Cohen, K. A. Scheidt, Chem. Sci. 2012, 3, 53
16. J. Douglas, G. Churchill, A. D. Smith, Synthesis 2012, 44, 2295
17. H. U. Vora, P. Wheeler, T. Rovis, Adv. Synth. Catal. 2012, 354, 1617
18. A. Grossmann, D. Enders, Angew. Chem. 2012, 124, 320
19. Angew. Chem. Int. Ed. 2012, 51, 314
20. X. Bugaut, F. Glorius, Chem. Soc. Rev. 2012, 41, 3511
21. M. Fèvre, J. Pinaud, Y. Gnanou, J. Vignolle, D. Taton, Chem. Soc. Rev. 2013, 42, 2142
22. S. J. Ryan, L. Candish, D. W. Lupton, Chem. Soc. Rev. 2013, 42, 4906
23. J. Mahatthananchai, J. W. Bode, Acc. Chem. Res. 2014, 47, 696
24. M. N. Hopkinson, C. Richter, M. Schedler, F. Glorius, Nature 2014, 510, 485.
25. S. S. Sohn, E. L. Rosen, J. W. Bode, J. Am. Chem. Soc. 2004, 126, 14370.
26. C. Burstein, F. Glorius, Angew. Chem. 2004, 116, 6331
27. Angew. Chem. Int. Ed. 2004, 43, 6205.
28. V. Nair, S. Vellalath, M. Poonoth, R. Mohan, E. Suresh, Org. Lett. 2006, 8, 507
29. C. Burstein, S. Tschan, X. L. Xie, F. Glorius, Synthesis 2006, 2418
30. K. Hirano, I. Piel, F. Glorius, Adv. Synth. Catal. 2008, 350, 984
31. Y. Li, Z.-A. Zhao, H. He, S.-L. You, Adv. Synth. Catal. 2008, 350, 1885
32. L.-H. Sun, L.-T. Shen, S. Ye, Chem. Commun. 2011, 47, 10136
33. J. Dugal-Tessier, E. A. O'Bryan, T. B. H. Schroeder, D. T. Cohen, K. A. Scheidt, Angew. Chem. 2012, 124, 5047
34. Angew. Chem. Int. Ed. 2012, 51, 4963
35. K. P. Jang, G. E. Hutson, R. C. Johnston, E. O. McCusker, H.-Y. Cheong, K. A. Scheidt, J. Am. Chem. Soc. 2014, 136, 76.
36. M. He, J. W. Bode, Org. Lett. 2005, 7, 3131
37. D. E. A. Raup, B. Cardinal-David, D. Holte, K. A. Scheidt, Nat. Chem. 2010, 2, 766
38. X. Zhao, D. A. DiRocco, T. Rovis, J. Am. Chem. Soc. 2011, 133, 12466
39. M. Rommel, T. Fukuzumi, J. W. Bode, J. Am. Chem. Soc. 2008, 130, 17266
40. B. Zhang, P. Feng, L.-H. Sun, Y. Cui, S. Ye, N. Jiao, Chem. Eur. J. 2012, 18, 9198
41. H. Lv, B. Tiwari, J. Mo, C. Xing, Y. R. Chi, Org. Lett. 2012, 14, 5412
42. A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 5334.
43. For NHC-homoenolate annulations of nitrones, see:, E. M. Phillips, T. E. Reynolds, K. A. Scheidt, J. Am. Chem. Soc. 2008, 130, 2416.
44. V. Nair, S. Vellalath, M. Poonoth, E. Suresh, J. Am. Chem. Soc. 2006, 128, 8736
45. P.-C. Chiang, J. Kaeobamrung, J. W. Bode, J. Am. Chem. Soc. 2007, 129, 3520
46. J. Kaeobamrung, J. W. Bode, Org. Lett. 2009, 11, 677
47. M. He, J. W. Bode, J. Am. Chem. Soc. 2008, 130, 418
48. K. Jiang, B. Tiwari, Y. R. Chi, Org. Lett. 2012, 14, 2382
49. X. Chen, X. Fang, Y. R. Chi, Chem. Sci. 2013, 4, 2613
50. V. Nair, M. Poonoth, S. Vellalath, E. Suresh, R. Thirumalai, J. Org. Chem. 2006, 71, 8964
51. D. Cohen, B. Cardinal-David, K. A. Scheidt, Angew. Chem. 2011, 123, 1716
52. Angew. Chem. Int. Ed. 2011, 50, 1678
53. X. Fang, K. Jiang, C. Xing, L. Hao, Y. R. Chi, Angew. Chem. 2011, 123, 1950
54. Angew. Chem. Int. Ed. 2011, 50, 1910
55. Z. Fu, J. Xu, T. Zhu, W. W. Y. Leong, Y. R. Chi, Nat. Chem. 2013, 5, 835.
56. N. T. Reynolds, J. R. D. Alaniz, T. Rovis, J. Am. Chem. Soc. 2004, 126, 9518
57. N. T. Reynolds, T. Rovis, J. Am. Chem. Soc. 2005, 127, 16406
58. H. U. Vora, T. Rovis, J. Am. Chem. Soc. 2007, 129, 13796
59. V. Nair, C. R. Sinu, B. P. Babu, V. Varghese, A. Jose, E. Suresh, Org. Lett. 2009, 11, 5570
60. H. U. Vora, T. Rovis, J. Am. Chem. Soc. 2010, 132, 2860
61. B. Maji, L. Ji, S. Wang, S. Vedachalam, G. Rakesh, X.-W. Liu, Angew. Chem. 2012, 124, 8401
62. Angew. Chem. Int. Ed. 2012, 51, 8276
63. P. Wheeler, H. U. Vora, T. Rovis, Chem. Sci. 2013, 4, 1674
64. N. A. White, D. A. DiRocco, T. Rovis, J. Am. Chem. Soc. 2013, 135, 8504.
65. V. Nair, B. P. Babu, S. Vellalath, E. Suresh, Chem. Commun. 2008, 747
66. J. R. Struble, J. Kaeobamrung, J. W. Bode, Org. Lett. 2008, 10, 957.
67. J. Izquierdo, A. Orue, K. A. Scheidt, J. Am. Chem. Soc. 2013, 135, 10634.
68. H. Lv, W.-Q. Jia, L.-H. Sun, S. Ye, Angew. Chem. 2013, 125, 8769
69. Angew. Chem. Int. Ed. 2013, 52, 8607.
70. P. S. Steyn, Tetrahedron Lett. 1971, 12, 3331
71. R. M. Williams, R. J. Cox, Acc. Chem. Res. 2003, 36, 127
72. G. Laus, Phytother. Res. 2004, 18, 259
73. S.-M. Li, Nat. Prod. Rep. 2010, 27, 57
74. M. E. Rateb, R. Ebel, Nat. Prod. Rep. 2011, 28, 290
75. F. Wang, Y. Fang, T. Zhu, M. Zhang, A. Lin, Q. Gu, W. Zhu, Tetrahedron 2008, 64, 7986
76. J. Sun, D. Shi, M. Ma, S. Li, S. Wang, L. Han, Y. Yang, X. Fan, J. Shi, L. He, J. Nat. Prod. 2005, 68, 915.
77. A. J. Birch, J. J. Wright, Chem. Commun. 1969, 644b
78. A. J. Birch, R. A. Russell, Tetrahedron 1972, 28, 2999.
79. R. R. M. Paterson, M. J. S. Simmonds, C. Kemmelmeier, W. M. Blaney, Mycol. Res. 1990, 94, 538.
80. K. Fuji, Chem. Rev. 1993, 93, 2037
81. C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363
82. B. M. Trost, D. C. Jiang, Synthesis 2006, 369.
83. J. B. Patrick, B. Witkop, J. Am. Chem. Soc. 1950, 72, 633
84. B. Witkop, J. Am. Chem. Soc. 1950, 72, 614
85. N. Finch, C. W. Gemenden, I. H.-C. Hsu, A. Kerr, G. A. Sim, W. I. Taylor, J. Am. Chem. Soc. 1965, 87, 2229
86. D. D. O'Rell, F. G. H. Lee, V. Boekelheide, J. Am. Chem. Soc. 1972, 94, 3205
87. F. C. Frebault, N. S. Simpkins, Tetrahedron 2010, 66, 6585
88. Y.-Q. Zhang, D.-Y. Zhu, Z.-W. Jiao, B.-S. Li, F.-M. Zhang, Y.-Q. Tu, Z. Bi, Org. Lett. 2011, 13, 3458
89. Y. Goriya, C. V. Ramana, Chem. Commun. 2013, 49, 6376
90. J.-B. Peng, Y. Qi, A.-J. Ma, Y.-Q. Tu, F.-M. Zhang, S.-H. Wang, S.-Y. Zhang, Chem. Asian J. 2013, 8, 883.
91. A. Buzas, J. Y. Merour, Synthesis 1989, 458.
92. CCDC 1001213 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.
93. P. Verma, P. A. Patni, R. B. Sunoj, J. Org. Chem. 2011, 76, 5606
94. H. Sun, X. Fang, Y. R. Chi, G. Li, Chirality 2013, 25, 521
95. E. O. McCusker, K. A. Scheidt, Angew. Chem. 2013, 125, 13861
96. Angew. Chem. Int. Ed. 2013, 52, 13616
97. D. S. IIIera, S. Suresh, M. Moccia, G. Bellini, M. Saviano, M. F. A. Adamo, Tetrahedron lett. 2012, 53, 1808
98. L. R. Domingo, J. A. Sáez, M. Arnõ, Org. Biomol. Chem. 2014, 12, 895
99. L.-T. Shen, W.-Q. Jia, S. Ye, Angew. Chem. 2013, 125, 613
100. Angew. Chem. Int. Ed. 2013, 52, 585.