Enantioselective all-carbon (4+2) annulation by N -heterocyclic carbene catalysis

Journal of the American Chemical Society

Volumn 136, Issue 41, 2014, Pages 14397-14400

  Candish, Lisa ^a   Levens, Alison ^a   Lupton, David W ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ESTERS; ISOMERIZATION;

CYCLOISOMERIZATIONS; DERIVATIZATIONS; DIASTEREOSELECTIVE; ENANTIOSELECTIVE; MECHANISTIC STUDIES; N-HETEROCYCLIC CARBENES; OLEFIN ISOMERIZATION; STEREOGENIC CENTERS;

ENANTIOSELECTIVITY;

BETA LACTONE; CARBENE; CARBON; HETEROCYCLIC COMPOUND; LACTONE DERIVATIVE; UNCLASSIFIED DRUG; CYCLOHEXENE DERIVATIVE; METHANE;

ANNULATION REACTION; ARTICLE; CATALYSIS; CYCLIZATION; CYCLOISOMERIZATION; DERIVATIZATION; ENANTIOSELECTIVITY; ISOMERIZATION; LACTONIZATION; MICHAEL ADDITION; PROTON TRANSPORT; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CARBON; CATALYSIS; CYCLIZATION; CYCLOHEXENES; HETEROCYCLIC COMPOUNDS; METHANE; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84908374403     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja508542n     Document Type: Article

References (68)

1. Juhl, M.; Tanner, D. Chem. Soc. Rev. 2009, 38, 2983
2. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668
3. Du, H.; Ding, K. Handbook of Cyclization Reactions, Vol. 1; Wiley: Weinheim, 2010.
4. Gompper, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 312
5. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 212
6. Hong, B.-C.; Wu, M.-F.; Tseng, H.-C.; Liao, J.-H. Org. Lett. 2006, 8, 2217
7. de Figueiredo, R. M.; Fröhlich, R.; Christmann, M. Angew. Chem., Int. Ed. 2008, 47, 1450
8. Jiang, H.; Albrecht, L.; Jørgensen, K. A. Chem. Sci. 2013, 4, 2287
9. Linder, M.; Brinck, T. J. Org. Chem. 2012, 77, 6563 and references therein
10. For a review discussing the challenges of vinylogous reactivity, see: Schneider, C.; Abels, F. Org. Biomol. Chem. 2014, 12, 3531
11. For an alternate NHC-catalyzed approach to the cyclohexyl β-lactone motif, see: Bera, S.; Samanta, R. C.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2014, 53, 9622
12. Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature 2014, 510, 485
13. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606
14. Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011, 40, 5336
15. Vora, H. U.; Wheeler, P.; Rovis, T. Adv. Synth. Catal. 2012, 354, 1617
16. Douglas, J.; Churchill, G.; Smith, A. D. Synthesis 2012, 44, 2295
17. Mahatthananchai, J.; Bode, J. W. Acc. Chem. Res. 2014, 47, 696
18. Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314
19. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511
20. Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 11686
21. Ryan, S. J.; Candish, L.; Lupton, D. W. Chem. Soc. Rev. 2013, 42, 4906
22. Morrill, L. C.; Smith, A. D. Chem. Soc. Rev. 2014, 43, 6214
23. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2009, 131, 14176
24. Candish, L.; Lupton, D. W. Org. Lett. 2010, 12, 4836
25. Candish, L.; Lupton, D. W. Org. Biomol. Chem. 2011, 9, 8182
26. Candish, L.; Lupton, D. W. Chem. Sci. 2012, 3, 380
27. Kowalczyk, M.; Lupton, D. W. Angew. Chem., Int. Ed. 2014, 53, 5314
28. Hao, L.; Du, Y.; Lv, H.; Chen, X.; Jiang, H.; Shao, Y.; Chi, Y. R. Org. Lett. 2012, 14, 2154
29. Hao, L.; Chen, S.; Xu, J.; Tiwari, B.; Fu, Z.; Li, T.; Lim, J.; Chi, Y. R. Org. Lett. 2013, 15, 4956
30. Chen, S.; Hao, L.; Zhang, Y.; Tiwari, B.; Chi, Y. R. Org. Lett. 2013, 15, 5822
31. Fu, Z.; Xu, J.; Zhu, T.; Leong, W. W. Y.; Chi, Y. R. Nat. Chem. 2013, 5, 835
32. Xu, J.; Jin, Z.; Chi, Y. R. Org. Lett. 2013, 15, 5028
33. Lee, A.; Younai, A.; Price, C. K.; Izquierdo, J.; Mishra, R. K.; Scheidt, K. A. J. Am. Chem. Soc. 2014, 136, 10589
34. Chen, X.-Y.; Gao, Z.-H.; Song, C.-Y.; Zhang, C.-L.; Wang, Z.-X.; Ye, S. Angew. Chem., Int. Ed. 2014, 10.1002/anie.201407469
35. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2011, 133, 4694
36. Ryan, S. J.; Stasch, A.; Paddon-Row, M. N.; Lupton, D. W. J. Org. Chem. 2012, 77, 1113
37. Tiseni, P. S.; Peters, R. Angew. Chem., Int. Ed. 2007, 46, 5325
38. Shen, L.-T.; Shao, P.-L.; Ye, S. Adv. Synth. Catal. 2011, 353, 1943
39. Mo, J.; Chen, X.; Chi, Y. R. J. Am. Chem. Soc. 2012, 134, 8810
40. Xiao, Z.; Yu, C.; Li, T.; Wang, X.-S.; Yao, C. Org. Lett. 2014, 16, 3632
41. Seeman, J. I. Chem. Rev. 1983, 83, 83
42. Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746
43. Burés, J.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2012, 134, 6741
44. Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 6940
45. Maji, B.; Breugst, M.; Mayr, H. Angew. Chem., Int. Ed. 2011, 50, 6915
46. Mahatthananchai, J.; Zheng, P.; Bode, J. W. Angew. Chem., Int. Ed. 2011, 50, 1673
47. Samanta, R. C.; Maji, B.; De Sarkar, S.; Bergander, K.; Fröhlich, R.; Mück-Lichtenfeld, C.; Mayr, H.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 5234
48. Zeitler, K. Org. Lett. 2006, 8, 637
49. Maki, B. E.; Chan, A.; Phillips, E. M.; Scheidt, K. A. Org. Lett. 2007, 9, 371
50. Reference 6a.
51. Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. J. Am. Chem. Soc. 2010, 132, 8810
52. De Sarkar, S.; Studer, A. Angew. Chem., Int. Ed. 2010, 49, 9266
53. Sun, F.-G.; Sun, L.-H.; Ye, S. Adv. Synth. Catal. 2011, 353, 3134
54. Candish, L.; Forsyth, C. M.; Lupton, D. W. Angew. Chem., Int. Ed. 2013, 52, 9149
55. Levens, A.; Candish, L.; Forsyth, C. M.; Lupton, D. W., unpublished.
56. Rovis, T. Chem. Lett. 2008, 37, 2
57. Mahatthananchai, J.; Bode, J. W. Chem. Sci. 2012, 3, 192
58. Reference 14a.
59. The role of salts in NHC organocatalysis has been documented previously by ourselves and others. For cooperative catalysis using Lewis acids and nucleophilic carbenes, see: Cohen, D. T.; Scheidt, K. A. Chem. Sci. 2012, 3, 53 and references therein
60. Burstein, C.; Tschan, S.; Xie, X.; Glorius, F. Synthesis 2006, 2418
61. Nair, V.; Vellalath, S.; Poonoth, M.; Suresh, E. J. Am. Chem. Soc. 2006, 128, 8736
62. Chiang, P.-C.; Kaeobamrung, J.; Bode, J. W. J. Am. Chem. Soc. 2007, 129, 3520
63. Wadamoto, M.; Phillips, E. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 10098
64. He, M.; Bode, J. W. J. Am. Chem. Soc. 2008, 130, 418
65. Kaeobamrung, J.; Bode, J. W. Org. Lett. 2009, 11, 677
66. Phillips, E. M.; Roberts, J. M.; Scheidt, K. A. Org. Lett. 2010, 12, 2830
67. Cohen, D. T.; Eichman, C. C.; Phillips, E. M.; Zarefsky, E. R.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 7309
68. For recent synthetic and computational studies covering NHC β-lactonization, see: Johnston, R. C.; Cohen, D. T.; Eichman, C. C.; Scheidt, K. A.; Cheong, P. H. Y. Chem. Sci. 2014, 5, 1974