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Angewandte Chemie - International Edition

Volumn 52, Issue 8, 2013, Pages 2212-2216

Synthesis of pyridines by carbenoid-mediated ring opening of 2H-azirines

(4) Loy, Nicole S Y a Singh, Alok a Xu, Xianxiu a Park, Cheol Min a

a Nanyang Technological University (Singapore)

Author keywords

carbenoids; electrocyclic reactions; heterocycle; ring expansion; synthetic methods

Indexed keywords

CARBENOIDS; ELECTROCYCLIC REACTIONS; HETEROCYCLES; RING EXPANSION; SYNTHETIC METHODS;

REACTION INTERMEDIATES;

PYRIDINE;

EID: 84873909860 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201209301 Document Type: Article

Times cited : (133)

References (69)

1
- 84891566518
- Wiley, Hoboken
- A. F. Pozharskii, A. Soldatenkov, A. R. Katritzky, Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications, Wiley, Hoboken, 2011
- (2011) Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications
- Pozharskii, A.F.¹ Soldatenkov, A.² Katritzky, A.R.³

2
- 26844495371
- J. P. Michael, Nat. Prod. Rep. 2005, 22, 627-646
- (2005) Nat. Prod. Rep. , vol.22 , pp. 627-646
- Michael, J.P.¹

3
- 0033775563
- D. O'Hagan, Nat. Prod. Rep. 2000, 17, 435-446.
- (2000) Nat. Prod. Rep. , vol.17 , pp. 435-446
- O'Hagan, D.¹

4
- 84255178590
- K. Kral, M. Hapke, Angew. Chem. 2011, 123, 2482-2483
- (2011) Angew. Chem. , vol.123 , pp. 2482-2483
- Kral, K.¹ Hapke, M.²

5
- 79952268143
- Angew. Chem. Int. Ed. 2011, 50, 2434-2435
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 2434-2435

6
- 84868375511
- Wiley, Hoboken
- J. A. Joule, K. Mills, Heterocyclic Chemistry, Wiley, Hoboken, 2010, pp. 115-175
- (2010) Heterocyclic Chemistry , pp. 115-175
- Joule, J.A.¹ Mills, K.²

7
- 78249271716
- M. D. Hill, Chem. Eur. J. 2010, 16, 12052-12062
- (2010) Chem. Eur. J. , vol.16 , pp. 12052-12062
- Hill, M.D.¹

8
- 84906465557
- in (Eds.: A. R. Katritzky, A. R. Christopher, E. F. V. Scriven, R. J. K. Taylor), Elsevier, Oxford
- P. A. Keller, in Comprehensive Heterocyclic Chemistry III, Vol. 7 (Eds.:, A. R. Katritzky, A. R. Christopher, E. F. V. Scriven, R. J. K. Taylor,), Elsevier, Oxford, 2008, pp. 217-308
- (2008) Comprehensive Heterocyclic Chemistry III, Vol. 7 , pp. 217-308
- Keller, P.A.¹

9
- 3042558198
- G. D. Henry, Tetrahedron 2004, 60, 6043-6061.
- (2004) Tetrahedron , vol.60 , pp. 6043-6061
- Henry, G.D.¹

10
- 11144310072
- C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 4957-4980
- (2004) Eur. J. Org. Chem. , pp. 4957-4980
- Simon, C.¹ Constantieux, T.² Rodriguez, J.³

11
- 0002407606
- A. Sausins, G. Duburs, Heterocycles 1988, 27, 269-289.
- (1988) Heterocycles , vol.27 , pp. 269-289
- Sausins, A.¹ Duburs, G.²

12
- 77953295929
- I. Nakamura, D. Zhang, M. Terada, J. Am. Chem. Soc. 2010, 132, 7884-7886
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 7884-7886
- Nakamura, I.¹ Zhang, D.² Terada, M.³

13
- 77957137428
- T. Sakai, R. L. Danheiser, J. Am. Chem. Soc. 2010, 132, 13203-13205
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 13203-13205
- Sakai, T.¹ Danheiser, R.L.²

14
- 73949123899
- F. Sha, X. Huang, Angew. Chem. 2009, 121, 3510-3513
- (2009) Angew. Chem. , vol.121 , pp. 3510-3513
- Sha, F.¹ Huang, X.²

15
- 70349783775
- Angew. Chem. Int. Ed. 2009, 48, 3458-3461
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 3458-3461

16
- 69849115537
- Y.-F. Wang, S. Chiba, J. Am. Chem. Soc. 2009, 131, 12570-12572
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 12570-12572
- Wang, Y.-F.¹ Chiba, S.²

17
- 44449138157
- S. Liu, L. S. Liebeskind, J. Am. Chem. Soc. 2008, 130, 6918-6919
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 6918-6919
- Liu, S.¹ Liebeskind, L.S.²

18
- 41449111035
- D. A. Colby, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2008, 130, 3645-3651
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 3645-3651
- Colby, D.A.¹ Bergman, R.G.² Ellman, J.A.³

19
- 40949147738
- J. Barluenga, M. Á. Fernández-Rodríguez, P. García-García, E. Aguilar, J. Am. Chem. Soc. 2008, 130, 2764-2765
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 2764-2765
- Barluenga, J.¹ Fernández-Rodríguez, M.A.² García- García, P.³ Aguilar, E.⁴

20
- 55449099596
- J. A. Varela, C. Saá, Synlett 2008, 2571-2578
- (2008) Synlett , pp. 2571-2578
- Varela, J.A.¹ Saá, C.²

21
- 34548146266
- M. Movassaghi, M. D. Hill, O. K. Ahmad, J. Am. Chem. Soc. 2007, 129, 10096-10097
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 10096-10097
- Movassaghi, M.¹ Hill, M.D.² Ahmad, O.K.³

22
- 33847030361
- H.-T. Chang, M. Jeganmohan, C.-H. Cheng, Org. Lett. 2007, 9, 505-508
- (2007) Org. Lett. , vol.9 , pp. 505-508
- Chang, H.-T.¹ Jeganmohan, M.² Cheng, C.-H.³

23
- 34250653953
- B. Heller, M. Hapke, Chem. Soc. Rev. 2007, 36, 1085-1094
- (2007) Chem. Soc. Rev. , vol.36 , pp. 1085-1094
- Heller, B.¹ Hapke, M.²

24
- 33646058040
- M. Movassaghi, M. D. Hill, J. Am. Chem. Soc. 2006, 128, 4592-4593
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 4592-4593
- Movassaghi, M.¹ Hill, M.D.²

25
- 17144426927
- M. M. McCormick, H. A. Duong, G. Zuo, J. Louie, J. Am. Chem. Soc. 2005, 127, 5030-5031
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 5030-5031
- McCormick, M.M.¹ Duong, H.A.² Zuo, G.³ Louie, J.⁴

26
- 19744370350
- D. Suzuki, Y. Nobe, Y. Watai, R. Tanaka, Y. Takayama, F. Sato, H. Urabe, J. Am. Chem. Soc. 2005, 127, 7474-7479
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 7474-7479
- Suzuki, D.¹ Nobe, Y.² Watai, Y.³ Tanaka, R.⁴ Takayama, Y.⁵ Sato, F.⁶ Urabe, H.⁷

27
- 0141677747
- J. A. Varela, C. Saá, Chem. Rev. 2003, 103, 3787-3802
- (2003) Chem. Rev. , vol.103 , pp. 3787-3802
- Varela, J.A.¹ Saá, C.²

28
- 0034820132
- Y. Yamamoto, R. Ogawa, K. Itoh, J. Am. Chem. Soc. 2001, 123, 6189-6190.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 6189-6190
- Yamamoto, Y.¹ Ogawa, R.² Itoh, K.³

29
- 80755129169
- B.-T. Guan, Z. Hou, J. Am. Chem. Soc. 2011, 133, 18086-18089
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 18086-18089
- Guan, B.-T.¹ Hou, Z.²

30
- 47749125841
- S. H. Cho, S. J. Hwang, S. Chang, J. Am. Chem. Soc. 2008, 130, 9254-9256
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 9254-9256
- Cho, S.H.¹ Hwang, S.J.² Chang, S.³

31
- 34247882697
- J. C. Lewis, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2007, 129, 5332-5333
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 5332-5333
- Lewis, J.C.¹ Bergman, R.G.² Ellman, J.A.³

32
- 15744362274
- K. Godula, B. Sezen, D. Sames, J. Am. Chem. Soc. 2005, 127, 3648-3649
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 3648-3649
- Godula, K.¹ Sezen, B.² Sames, D.³

33
- 2942530950
- R. Chinchilla, C. Nájera, M. Yus, Chem. Rev. 2004, 104, 2667-2722.
- (2004) Chem. Rev. , vol.104 , pp. 2667-2722
- Chinchilla, R.¹ Nájera, C.² Yus, M.³

34
- 78651311337
- M. Murakami, T. Matsuda, Chem. Commun. 2011, 47, 1100-1105
- (2011) Chem. Commun. , vol.47 , pp. 1100-1105
- Murakami, M.¹ Matsuda, T.²

35
- 70350512114
- C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, 3051-3060
- (2009) Chem. Soc. Rev. , vol.38 , pp. 3051-3060
- Carson, C.A.¹ Kerr, M.A.²

36
- 11844273927
- C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610-618.
- (2004) Chem. Soc. Rev. , vol.33 , pp. 610-618
- Jun, C.-H.¹

37
- 67749106330
- A. T. Parsons, J. S. Johnson, J. Am. Chem. Soc. 2009, 131, 3122-3123
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 3122-3123
- Parsons, A.T.¹ Johnson, J.S.²

38
- 67849092152
- D. C. Moebius, J. S. Kingsbury, J. Am. Chem. Soc. 2009, 131, 878-879
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 878-879
- Moebius, D.C.¹ Kingsbury, J.S.²

39
- 60949091510
- H. Xu, W. Zhang, D. Shu, J. B. Werness, W. Tang, Angew. Chem. 2008, 120, 9065-9068
- (2008) Angew. Chem. , vol.120 , pp. 9065-9068
- Xu, H.¹ Zhang, W.² Shu, D.³ Werness, J.B.⁴ Tang, W.⁵

40
- 57349182690
- Angew. Chem. Int. Ed. 2008, 47, 8933-8936
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 8933-8936

41
- 70349948611
- T. Seiser, N. Cramer, Angew. Chem. 2008, 120, 9435-9438
- (2008) Angew. Chem. , vol.120 , pp. 9435-9438
- Seiser, T.¹ Cramer, N.²

42
- 56449094610
- Angew. Chem. Int. Ed. 2008, 47, 9294-9297
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 9294-9297

43
- 35549010707
- T. Matsuda, T. Tsuboi, M. Murakami, J. Am. Chem. Soc. 2007, 129, 12596-12597
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 12596-12597
- Matsuda, T.¹ Tsuboi, T.² Murakami, M.³

44
- 22144454984
- J. P. Markham, S. T. Staben, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 9708-9709.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 9708-9709
- Markham, J.P.¹ Staben, S.T.² Toste, F.D.³

45
- 84863229529
- Y. Jiang, W. C. Chan, C.-M. Park, J. Am. Chem. Soc. 2012, 134, 4104-4107
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 4104-4107
- Jiang, Y.¹ Chan, W.C.² Park, C.-M.³

46
- 77955158272
- D. A. Candito, M. Lautens, Org. Lett. 2010, 12, 3312-3315
- (2010) Org. Lett. , vol.12 , pp. 3312-3315
- Candito, D.A.¹ Lautens, M.²

47
- 77956208728
- S. Jana, M. D. Clements, B. K. Sharp, N. Zheng, Org. Lett. 2010, 12, 3736-3739
- (2010) Org. Lett. , vol.12 , pp. 3736-3739
- Jana, S.¹ Clements, M.D.² Sharp, B.K.³ Zheng, N.⁴

48
- 40949115103
- S. Brahma, J. K. Ray, J. Heterocycl. Chem. 2008, 45, 311-317
- (2008) J. Heterocycl. Chem. , vol.45 , pp. 311-317
- Brahma, S.¹ Ray, J.K.²

49
- 31944441649
- D. F. Taber, W. Tian, J. Am. Chem. Soc. 2006, 128, 1058-1059
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 1058-1059
- Taber, D.F.¹ Tian, W.²

50
- 27144513812
- K. L. Stevens, D. K. Jung, M. J. Alberti, J. G. Badiang, G. E. Peckham, J. M. Veal, M. Cheung, P. A. Harris, S. D. Chamberlain, M. R. Peel, Org. Lett. 2005, 7, 4753-4756
- (2005) Org. Lett. , vol.7 , pp. 4753-4756
- Stevens, K.L.¹ Jung, D.K.² Alberti, M.J.³ Badiang, J.G.⁴ Peckham, G.E.⁵ Veal, J.M.⁶ Cheung, M.⁷ Harris, P.A.⁸ Chamberlain, S.D.⁹ Peel, M.R.¹⁰

51
- 3142684571
- A. Padwa, T. Stengel, Tetrahedron Lett. 2004, 45, 5991-5993.
- (2004) Tetrahedron Lett. , vol.45 , pp. 5991-5993
- Padwa, A.¹ Stengel, T.²

52
- 84866666954
- X. Zhao, Y. Zhang, J. Wang, Chem. Commun. 2012, 48, 10162-10173
- (2012) Chem. Commun. , vol.48 , pp. 10162-10173
- Zhao, X.¹ Zhang, Y.² Wang, J.³

53
- 84856505982
- F. de C. da Silva, A. K. Jordao, D. R. da Rocha, S. B. Ferreira, A. C. Cunha, V. F. Ferreira, Curr. Org. Chem. 2012, 16, 224-251
- (2012) Curr. Org. Chem. , vol.16 , pp. 224-251
- Da Silva, F.D.C.¹ Jordao, A.K.² Da Rocha, D.R.³ Ferreira, S.B.⁴ Cunha, A.C.⁵ Ferreira, V.F.⁶

54
- 80054734190
- X. Wang, X. Xu, P. Y. Zavalij, M. P. Doyle, J. Am. Chem. Soc. 2011, 133, 16402-16405
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 16402-16405
- Wang, X.¹ Xu, X.² Zavalij, P.Y.³ Doyle, M.P.⁴

55
- 65649131752
- in (Ed.: A. Hassner), Springer, Berlin
- S. Muthusamy, J. Krishnamurthi, in Synthesis of Heterocycles via Cycloadditions I, Vol. 12 (Ed.:, A. Hassner,), Springer, Berlin, 2008, pp. 147-192
- (2008) Synthesis of Heterocycles Via Cycloadditions I, Vol. 12 , pp. 147-192
- Muthusamy, S.¹ Krishnamurthi, J.²

56
- 46949086690
- J. R. Manning, H. M. L. Davies, J. Am. Chem. Soc. 2008, 130, 8602-8603
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 8602-8603
- Manning, J.R.¹ Davies, H.M.L.²

57
- 34250021382
- A. Padwa, S. K. Bur, Tetrahedron 2007, 63, 5341-5378
- (2007) Tetrahedron , vol.63 , pp. 5341-5378
- Padwa, A.¹ Bur, S.K.²

58
- 34548219536
- R. P. Reddy, H. M. L. Davies, J. Am. Chem. Soc. 2007, 129, 10312-10313
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 10312-10313
- Reddy, R.P.¹ Davies, H.M.L.²

59
- 33845969195
- V. F. Ferreira, Curr. Org. Chem. 2007, 11, 177-193
- (2007) Curr. Org. Chem. , vol.11 , pp. 177-193
- Ferreira, V.F.¹

60
- 0037462078
- M. P. Doyle, M. Yan, W. Hu, L. S. Gronenberg, J. Am. Chem. Soc. 2003, 125, 4692-4693.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 4692-4693
- Doyle, M.P.¹ Yan, M.² Hu, W.³ Gronenberg, L.S.⁴

61
- 84859140048
- X. Qi, X. Xu, C.-M. Park, Chem. Commun. 2012, 48, 3996-3998
- (2012) Chem. Commun. , vol.48 , pp. 3996-3998
- Qi, X.¹ Xu, X.² Park, C.-M.³

62
- 84865708929
- E. Lourdusamy, L. Yao, C.-M. Park, Angew. Chem. 2010, 122, 8135-8139
- (2010) Angew. Chem. , vol.122 , pp. 8135-8139
- Lourdusamy, E.¹ Yao, L.² Park, C.-M.³

63
- 78349243665
- Angew. Chem. Int. Ed. 2010, 49, 7963-7967.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 7963-7967

64
- 77953870231
- Wiley, Hoboken.
- Z. Rappoport, J. F. Liebman, The chemistry of hydroxylamines, oximes and hydroxamic acids, Vol. 2, Wiley, Hoboken, 2008.
- (2008) The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids, Vol. 2
- Rappoport, Z.¹ Liebman, J.F.²

65
- 84873932870
- CCDC 911613 (4 ba) 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.

66
- 9644254037
- C. G. Espino, K. W. Fiori, M. Kim, J. Du Bois, J. Am. Chem. Soc. 2004, 126, 15378-15379.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 15378-15379
- Espino, C.G.¹ Fiori, K.W.² Kim, M.³ Du Bois, J.⁴

67
- 34248578376
- Y. Shirota, H. Kageyama, Chem. Rev. 2007, 107, 953-1010
- (2007) Chem. Rev. , vol.107 , pp. 953-1010
- Shirota, Y.¹ Kageyama, H.²

68
- 0043098202
- R. L. Carroll, C. B. Gorman, Angew. Chem. 2002, 114, 4556-4579
- (2002) Angew. Chem. , vol.114 , pp. 4556-4579
- Carroll, R.L.¹ Gorman, C.B.²

69
- 0037011210
- Angew. Chem. Int. Ed. 2002, 41, 4378-4400.
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4378-4400

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