N-heterocyclic carbene (NHC)-catalyzed all-carbon [4+2] cycloaddition-decarboxylation

Synlett

Volumn , Issue 16, 2011, Pages 2275-2278

  Ryan, Sarah ^a   Candish, Lisa ^a   Lupton, David W ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

acyl azolium; catalysis; cycloaddition; cyclohexadiene; N heterocyclic carbenes

Indexed keywords

CARBENE; N HETEROCYCLIC CARBENE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; DECARBOXYLATION; DIELS ALDER REACTION; OXIDATION; SYNTHESIS;

EID: 80053100808     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1261226     Document Type: Article

References (70)

1. Ugai T, Tanaka S, Dokawa S, J. Pharm. Soc. Jpn. 1943 63 296
2. Breslow R, J. Am. Chem. Soc. 1958 80 3719
3. For reviews on NHC catalysis, see:, Enders D, Niemeier O, Henseler A, Chem. Rev. 2007 107 5606
4. Marion N, Díez-González S, Nolan S P., Angew. Chem. Int. Ed. 2007 46 2988
5. Nair V, Vellalath S, Babu B P., Chem. Soc. Rev. 2008 37 2691
6. Moore J L., Rovis T, Top. Curr. Chem. 2009 290 77
7. Phillips E M., Chan A, Scheidt K A., Aldrichimica Acta 2009 42 55
8. Vora H H., Rovis T, Aldrichimica Acta 2011 44 3
9. Castells J, Llitjos H, Moreno-Maas M, Tetrahedron Lett. 1977 18 205
10. For examples with cyanide, see:, Corey E J., Gilman N W., Ganem R E., J. Am. Chem. Soc. 1968 90 5616
11. Corey E J., Katzenellenbogen J A., Gilman N W., Roman S A., Erickson B W., J. Am. Chem. Soc. 1968 90 5618
12. For other examples of oxidations of acyl anions to acyl azoliums, see:, Ohta S, Hayakawa S, Nishimura K, Okamoto M, Chem. Pharm. Bull. 1987 135 1058
13. Miyashita A, Suzuki Y, Nagasaki I, Iwamoto K.-I, Higashino T, Chem. Pharm. Bull. 1997 45 1254
14. For examples of acyl azolium catalysis, see
15. Chow K Y.-K, Bode J W., J. Am. Chem. Soc. 2004 126 8126
16. Reynolds N T., ReaddeAlaniz J, Rovis T, J. Am. Chem. Soc. 2004 126 9518
17. Burstein C, Glorius F, Angew. Chem. Int. Ed. 2004 43 6205
18. Sohn S S., Rosen E L., Bode J W., J. Am. Chem. Soc. 2004 126 14370
19. Chan A, Scheidt K A., Org. Lett. 2005 7 905
20. Zeitler K, Org. Lett. 2006 8 637
21. Maki B E., Chan A, Phillips E M., Scheidt K A., Org. Lett. 2007 9 371
22. Vora H U., Rovis T, J. Am. Chem. Soc. 2007 129 13796
23. Guin J, De Sarkar S, Grimme S, Studer A, Angew. Chem. Int. Ed. 2008 47 8727
24. Maki B E., Patterson E V., Cramer C J., Scheidt K A., Org. Lett. 2009 11 3942
25. Philips E M., Wadamoto M, Roth H S., Ott A W., Scheidt K A., Org. Lett. 2009 11 105
26. Vora H U., Rovis T, J. Am. Chem. Soc. 2010 132 2860
27. De Sarkar S, Grimme S, Studer A, J. Am. Chem. Soc. 2010 132 1190
28. Thai K, Wang L, Dudding T, Bilodeau F, Gravel M, Org. Lett. 2010 12 5708
29. De Sarkar S, Studer A, Org. Lett. 2010 12 1992
30. De Sarkar S, Biswas A, Song C H., Studer A, Synthesis 2011 1974
31. For a review on Lewis base catalysis, see:, Denmark S E., Beutner G L., Angew. Chem. Int. Ed. 2008 47 1560
32. For reviews on NHC nucleophilicity, see:, Mayr H, Breugst M, Maji B, Angew. Chem. Int. Ed. 2011 50 6915
33. Dröge T, Glorius F, Angew. Chem. Int. Ed. 2010 49 6940
34. For the Mukaiyama aldol reaction, see:, Song J J., Tan Z, Reeves J T., Yee N K., Senanayake C H., Org. Lett. 2007 9 1013; for other examples of C-Si activation, see articles cited therein
35. Lee K.-S, Zhugralin A R., Hoveyda A H., J. Am. Chem. Soc. 2009 131 7253
36. Fischer C, Smith S W., Powell D A., Fu G C., J. Am. Chem. Soc. 2006 128 1472 For recent extentions of this type of reactivity, see:, Matsuoka S I., Ota Y, Washio A, Katada A, Ichioka K, Takagi K, Suzuki M, Org. Lett. 2011 13 3722
37. Biju A T., Padmanaban M, Wurz N E., Glorius F, Angew. Chem. Int. Ed. 2011 50 DOI: 10.1002/anie.201103555
38. Grasa G A., Kissling R M., Nolan S P., Org. Lett. 2002 4 3583
39. Nyce G W., Lamboy J A., Connor E F., Waymouth R M., Hedrick J L., Org. Lett. 2002 4 3587
40. Movassaghi M, Schmidt M A., Org. Lett. 2005 7 2453
41. Schmidt M A., Müller P, Movassaghi M, Tetrahedron Lett. 2008 49 4316
42. Song J J., Tan Z, Reeves J T., Fandrick D R., Yee N K., Senanayake C H., Org. Lett. 2008 10 877
43. Ryan S J., Candish L, Lupton D W., J. Am. Chem. Soc. 2009 131 14176
44. Candish L, Lupton D W., Org. Lett. 2010 12 4836
45. For a related reaction with mechanistic discussion, see:, Kaeobamrung J, Mahatthananchai J, Zheng P, Bode J W., J. Am. Chem. Soc. 2010 132 8810
46. Mahatthananchai J, Zheng P, Bode J W., Angew. Chem. Int. Ed. 2011 50 1673
47. For related reactions, see:, De Sarkar S, Studer A, Angew. Chem. Int. Ed. 2010 49 9266
48. Zhu Z.-Q, Xiao J.-C, Adv. Synth. Catal. 2010 352 2455
49. Zhu Z.-Q, Zheng X.-L, Jiang N.-F, Wan X, Xiao J.-C, Chem. Commun. 2011 47 8670
50. Rong Z.-Q, Jia M.-Q, You S.-L, Org. Lett. 2011 13 4080
51. Bappert E, Müller P, Fu G, Chem. Commun. 2006 2604
52. Poisson T, Dalla V, Papamicaël C, Dupas G, Marsais F, Levacher V, Synlett 2007 381
53. Woods P A., Morrill L C., Lebl T, Slawin A M. Z., Bragg R A., Smith A D., Org. Lett. 2010 12 2660
54. For NHC-catalyzed reactions involving -lactones, see:, Nair V, Vellalath S, Poonoth M, Suresh E, J. Am. Chem. Soc. 2006 128 8736
55. Chiang P.-C, Kaeobamrung J, Bode J W., J. Am. Chem. Soc. 2007 129 3520
56. Wadamoto M, Phillips E M., Reynolds T E., Scheidt K A., J. Am. Chem. Soc. 2007 129 10098
57. He M, Bode J W., J. Am. Chem. Soc. 2008 130 418
58. Kaeobamrung J, Bode J W., Org. Lett. 2009 11 677
59. Phillips E M., Roberts J M., Scheidt K A., Org. Lett. 2010 12 2830
60. For a useful review on 2-pyrones and 2-pyridones in synthesis, see
61. Afarinkia K, Vinader V, Nelson T D., Posner G H., Tetrahedron 1992 48 9111
62. Soh J Y.-T, Tan C H., J. Am. Chem. Soc. 2009 131 6904
63. Martin S F., Rüeger H, Williamson S A., Grzejszczak S, J. Am. Chem. Soc. 1987 109 6124
64. Nelson H M., Stoltz B M., Org. Lett. 2008 10 25
65. Baran P S., Burns N Z., J. Am. Chem. Soc. 2006 128 3908
66. Li L, Chase C E., West F G., Chem. Commun. 2008 4025
67. Afarinkia K, Abdullahi M H., Scowen I J., Org. Lett. 2010 12 5564
68. Ryan S J., Candish L, Lupton D W., J. Am. Chem. Soc. 2011 133 4694
69. Ryan, S. J.; Paddon-Row, M. Lupton, D. W. unpublished results.
70. For a review on vinylogous reactivity, see:, Denmark S E., Heemstra J R. Jr., Beutner G L., Angew. Chem. Int. Ed. 2005 44 4682