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Journal of the American Chemical Society

Volumn 136, Issue 29, 2014, Pages 10266-10269

Mild aminoacylation of indoles and pyrroles through a three-component reaction with ynol ethers and sulfonyl azides

(2) Alford, Joshua S a Davies, Huw M L a

a EMORY UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NITROGEN COMPOUNDS;

AMINOACYLATION; CASCADE REACTIONS; HIGH YIELD; MILD REACTION CONDITIONS; MULTICOMPONENTS; ONE POT; SULFONYL AZIDES; THREE COMPONENT REACTIONS;

ETHERS;

AZIDE; ETHER DERIVATIVE; INDOLE DERIVATIVE; OXYGEN; PYRROLE DERIVATIVE;

AMINOACYLATION; ARTICLE; CYCLOPROPANATION; MICROWAVE IRRADIATION; REACTION ANALYSIS; RING OPENING; SUBSTITUTION REACTION;

EID: 84904906746 PISSN: 00027863 EISSN: 15205126 Source Type: Journal
DOI: 10.1021/ja5058967 Document Type: Article

Times cited : (122)

References (62)

1
- 0041878773
- Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861-2903
- (2003) Chem. Rev. , vol.103 , pp. 2861-2903
- Davies, H.M.L.¹ Beckwith, R.E.J.²

2
- 0038222536
- Lebel, H.; Marcoux, J.; Carmela, M.; Charette, A. B. Chem. Rev. 2003, 103, 977-1050
- (2003) Chem. Rev. , vol.103 , pp. 977-1050
- Lebel, H.¹ Marcoux, J.² Carmela, M.³ Charette, A.B.⁴

3
- 38749146550
- Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417-424
- (2008) Nature , vol.451 , pp. 417-424
- Davies, H.M.L.¹ Manning, J.R.²

4
- 45849093273
- Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577-6605
- (2008) Tetrahedron , vol.64 , pp. 6577-6605
- Zhang, Z.¹ Wang, J.²

5
- 70350515235
- Davies, H. M. L.; Denton, J. R. Chem. Soc. Rev. 2009, 38, 3061-3071
- (2009) Chem. Soc. Rev. , vol.38 , pp. 3061-3071
- Davies, H.M.L.¹ Denton, J.R.²

6
- 77349105953
- Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704-724
- (2010) Chem. Rev. , vol.110 , pp. 704-724
- Doyle, M.P.¹ Duffy, R.² Ratnikov, M.³ Zhou, L.⁴

7
- 79959788014
- Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857-1869
- (2011) Chem. Soc. Rev. , vol.40 , pp. 1857-1869
- Davies, H.M.L.¹ Morton, D.²

8
- 80755158091
- De Vries, J. G. Molander, G. A. Evans, A. P. Thieme
- Davies, H. M. L.; Morton, D. Science of Synthesis, Stereoselective Synthesis; De Vries, J. G.; Molander, G. A.; Evans, A. P., Eds.; Thieme: 2011; Vol. 3, p 513.
- (2011) Science of Synthesis, Stereoselective Synthesis , vol.3 , pp. 513
- Davies, H.M.L.¹ Morton, D.²

9
- 84863470194
- Davies, H. M. L.; Lian, Y. Acc. Chem. Res. 2012, 45, 923-935
- (2012) Acc. Chem. Res. , vol.45 , pp. 923-935
- Davies, H.M.L.¹ Lian, Y.²

10
- 0034617206
- Panaro, S. A.; Davies, H. M. L. Tetrahedron 2000, 56, 4871-4880
- (2000) Tetrahedron , vol.56 , pp. 4871-4880
- Panaro, S.A.¹ Davies, H.M.L.²

11
- 0030796786
- Davies, H. M. L.; Hansen, J. J. Am. Chem. Soc. 1997, 119, 9075-9076
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 9075-9076
- Davies, H.M.L.¹ Hansen, J.²

12
- 0034607295
- Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063-3070
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 3063-3070
- Davies, H.M.L.¹ Hansen, T.² Churchill, M.R.³

13
- 0034731659
- Doyle, M. P.; Hu, W. J. Org. Chem. 2000, 65, 8839-8847
- (2000) J. Org. Chem. , vol.65 , pp. 8839-8847
- Doyle, M.P.¹ Hu, W.²

14
- 77950302895
- Bonge, H. T.; Hansen, T. J. Org. Chem. 2010, 75, 2309-2320
- (2010) J. Org. Chem. , vol.75 , pp. 2309-2320
- Bonge, H.T.¹ Hansen, T.²

15
- 84870937646
- Alford, J. S.; Davies, H. M. L. Org. Lett. 2012, 14, 6020-6023
- (2012) Org. Lett. , vol.14 , pp. 6020-6023
- Alford, J.S.¹ Davies, H.M.L.²

16
- 33646493950
- A single example of a methoxytrifluoromethylcarbene derived from 3-methoxy-3-trifluoromethyldiazirine has been reported; see: Moss, R. A.; Zdrojewski, T.; Ho, G. J. Chem. Soc., Chem. Commun. 1991, 946-947
- (1991) J. Chem. Soc., Chem. Commun. , pp. 946-947
- Moss, R.A.¹ Zdrojewski, T.² Ho, G.³

17
- 34347204116
- Chuprakov, S.; Hwang, F. W.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 4757-4759
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 4757-4759
- Chuprakov, S.¹ Hwang, F.W.² Gevorgyan, V.³

18
- 57349191194
- Horneff, T.; Chuprakov, S.; Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972-14974
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14972-14974
- Horneff, T.¹ Chuprakov, S.² Chernyak, N.³ Gevorgyan, V.⁴ Fokin, V.V.⁵

19
- 61849183666
- Miura, T.; Yamauchi, M.; Murakami, M. Chem. Commun. 2009, 1470-1471
- (2009) Chem. Commun. , pp. 1470-1471
- Miura, T.¹ Yamauchi, M.² Murakami, M.³

20
- 84855990688
- Chattopadhyay, B.; Gevorgyan, B. Angew. Chem., Int. Ed. 2012, 51, 862-872
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 862-872
- Chattopadhyay, B.¹ Gevorgyan, B.²

21
- 84872833141
- Gulevich, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2013, 52, 1371-1373
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 1371-1373
- Gulevich, A.V.¹ Gevorgyan, V.²

22
- 84903188730
- Davies, H. M. L.; Alford, J. S. Chem. Soc. Rev. 2014, 5151-5162
- (2014) Chem. Soc. Rev. , pp. 5151-5162
- Davies, H.M.L.¹ Alford, J.S.²

23
- 84872864965
- Zibinsky, M.; Fokin, V. V. Angew. Chem., Int. Ed. 2013, 52, 1507-1510
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 1507-1510
- Zibinsky, M.¹ Fokin, V.V.²

24
- 84875727243
- Parr, B. T.; Green, S. A.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 4716-4718
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 4716-4718
- Parr, B.T.¹ Green, S.A.² Davies, H.M.L.³

25
- 84875701371
- Schultz, E. E.; Sarpong, R. J. Am. Chem. Soc. 2013, 135, 4696-4699
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 4696-4699
- Schultz, E.E.¹ Sarpong, R.²

26
- 84875750598
- Chuprakov, S.; Kwok, S. W.; Fokin, V. V. J. Am. Chem. Soc. 2013, 135, 4652-4655
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 4652-4655
- Chuprakov, S.¹ Kwok, S.W.² Fokin, V.V.³

27
- 84877279503
- Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6802-6805
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 6802-6805
- Spangler, J.E.¹ Davies, H.M.L.²

28
- 84882272975
- Parr, B. T.; Davies, H. M. L. Angew. Chem., Int. Ed. 2013, 52, 10044-10047
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 10044-10047
- Parr, B.T.¹ Davies, H.M.L.²

29
- 84882262173
- Alford, J. S.; Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 11712-11715
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 11712-11715
- Alford, J.S.¹ Spangler, J.E.² Davies, H.M.L.³

30
- 84880004562
- Miura, T.; Hiraga, K.; Biyajima, T.; Nakamuro, T.; Murakami, M. Org. Lett. 2013, 15, 3298-3301
- (2013) Org. Lett. , vol.15 , pp. 3298-3301
- Miura, T.¹ Hiraga, K.² Biyajima, T.³ Nakamuro, T.⁴ Murakami, M.⁵

31
- 84884494498
- Miura, T.; Tanaka; Hiraga, K.; Stewart, S. G.; Murakami, M. J. Am. Chem. Soc. 2013, 135, 13652-13655
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 13652-13655
- Miura, T.¹ Tanaka² Hiraga, K.³ Stewart, S.G.⁴ Murakami, M.⁵

32
- 84886304031
- Shi, Y.; Gevorgyan, V. Org. Lett. 2013, 15, 5394-5396
- (2013) Org. Lett. , vol.15 , pp. 5394-5396
- Shi, Y.¹ Gevorgyan, V.²

33
- 84892181640
- Chuprakov, S.; Worrell, B. T.; Selander, N.; Sit, R. K.; Fokin, V. V. J. Am. Chem. Soc. 2014, 136, 195-202
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 195-202
- Chuprakov, S.¹ Worrell, B.T.² Selander, N.³ Sit, R.K.⁴ Fokin, V.V.⁵

34
- 84894115779
- Miura, T.; Funakoshi, Y.; Murakami, M. J. Am. Chem. Soc. 2014, 136, 2272-2275
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 2272-2275
- Miura, T.¹ Funakoshi, Y.² Murakami, M.³

35
- 84896483388
- Kwok, S. W.; Zhang, L.; Grimster, N. P.; Fokin, V. V. Angew. Chem., Int. Ed. 2014, 53, 3452-3456
- (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 3452-3456
- Kwok, S.W.¹ Zhang, L.² Grimster, N.P.³ Fokin, V.V.⁴

36
- 84896950279
- Boyer, A. Org. Lett. 2014, 16, 1660-1663
- (2014) Org. Lett. , vol.16 , pp. 1660-1663
- Boyer, A.¹

37
- 84898739783
- Kim, C.; Park, S.; Eom, D.; Seo, B.; Lee, P. H. Org. Lett. 2014, 16, 1900-1903
- (2014) Org. Lett. , vol.16 , pp. 1900-1903
- Kim, C.¹ Park, S.² Eom, D.³ Seo, B.⁴ Lee, P.H.⁵

38
- 84899004056
- Jung, D. J.; Jeon, H. J.; Kim, J. H.; Kim, Y.; Lee, S. Org. Lett. 2014, 16, 2208-2211
- (2014) Org. Lett. , vol.16 , pp. 2208-2211
- Jung, D.J.¹ Jeon, H.J.² Kim, J.H.³ Kim, Y.⁴ Lee, S.⁵

39
- 84899995236
- Yang, J.; Zhu, C.; Tang, X.; Shi, M. Angew. Chem., Int. Ed. 2014, 53, 5142-5146
- (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 5142-5146
- Yang, J.¹ Zhu, C.² Tang, X.³ Shi, M.⁴

40
- 0034607853
- Buron, C.; Gornitzka, H.; Romanenko, V.; Bertrand, G. Science 2000, 288, 834-836
- (2000) Science , vol.288 , pp. 834-836
- Buron, C.¹ Gornitzka, H.² Romanenko, V.³ Bertrand, G.⁴

41
- 39749200765
- Al-Rashid, Z. F.; Hsung, R. P. Org. Lett. 2008, 10, 661-663
- (2008) Org. Lett. , vol.10 , pp. 661-663
- Al-Rashid, Z.F.¹ Hsung, R.P.²

42
- 77954608063
- Li, H.; Antoline, J.; Yang, J.; Al-Rashid, Z.; Hsung, R. New J. Chem. 2010, 34, 1309-1316
- (2010) New J. Chem. , vol.34 , pp. 1309-1316
- Li, H.¹ Antoline, J.² Yang, J.³ Al-Rashid, Z.⁴ Hsung, R.⁵

43
- 84875750924
- We are aware of a single example of the use of a 4-alkoxy-1-tosyltriazole to generate carbene intermediates, involving a reaction with allylic alcohols under rhodium-catalyzed conditions. See: Miura, T.; Tanaka, T.; Biyajima, T.; Yada, A.; Murakami, M. Angew. Chem., Int. Ed. 2013, 52, 3883-3886
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 3883-3886
- Miura, T.¹ Tanaka, T.² Biyajima, T.³ Yada, A.⁴ Murakami, M.⁵

44
- 34250643020
- For a review on the reaction of metal carbenes with electron-rich heterocycles, see: Hedley, S. J.; Davies, H. M. L. Chem. Soc. Rev. 2007, 36, 1109-1119
- (2007) Chem. Soc. Rev. , vol.36 , pp. 1109-1119
- Hedley, S.J.¹ Davies, H.M.L.²

45
- 74949136287
- Lian, Y.; Davies, H. M. L. J. Am. Chem. Soc. 2010, 132, 440-441
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 440-441
- Lian, Y.¹ Davies, H.M.L.²

46
- 79951542336
- DeAngelis, A.; Shurtleff, V. W.; Dmitrenko, O.; Fox, J. M. J. Am. Chem. Soc. 2011, 133, 1650-1653
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 1650-1653
- Deangelis, A.¹ Shurtleff, V.W.² Dmitrenko, O.³ Fox, J.M.⁴

47
- 81555226820
- Yu, Z.; DeAngelis, A.; Cai, Y.; Zhu, S.; Wang, G.; Zhou, Q. Adv. Synth. Catal. 2011, 353, 2939-2944
- (2011) Adv. Synth. Catal. , vol.353 , pp. 2939-2944
- Yu, Z.¹ Deangelis, A.² Cai, Y.³ Zhu, S.⁴ Wang, G.⁵ Zhou, Q.⁶

48
- 84863533875
- Dmitrenko, O.; Fox, J. M. J. Am. Chem. Soc. 2012, 134, 11035-11043
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 11035-11043
- Dmitrenko, O.¹ Fox, J.M.²

49
- 84866843650
- Ma, B.; Qui, H. Q.; Li, M.; Jiang, L.; Lv, F.; Zan, L.; Zhai, C.; Doyle, M. P.; Hu, W. Nat. Chem. 2012, 4, 733-738
- (2012) Nat. Chem. , vol.4 , pp. 733-738
- Ma, B.¹ Qui, H.Q.² Li, M.³ Jiang, L.⁴ Lv, F.⁵ Zan, L.⁶ Zhai, C.⁷ Doyle, M.P.⁸ Hu, W.⁹

50
- 84900807376
- Chen, M.; Wu, H.; Liu, L.; Zhang, J. J. Am. Chem. Soc. 2014, 136, 6904-6907
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 6904-6907
- Chen, M.¹ Wu, H.² Liu, L.³ Zhang, J.⁴

51
- 84894527266
- Xing, Y.; Sheng, G.; Wang, J.; Lu, P.; Wang, Y. Org. Lett. 2014, 16, 1244-1247
- (2014) Org. Lett. , vol.16 , pp. 1244-1247
- Xing, Y.¹ Sheng, G.² Wang, J.³ Lu, P.⁴ Wang, Y.⁵

52
- 79960174547
- Mejuch, T.; Botoshansky, M.; Marek, I. Org. Lett. 2011, 13, 3604-3607
- (2011) Org. Lett. , vol.13 , pp. 3604-3607
- Mejuch, T.¹ Botoshansky, M.² Marek, I.³

53
- 80855156723
- Miyauchi, Y.; Kobayashi, M.; Tanaka, K. Angew. Chem., Int. Ed. 2011, 50, 10922-10926
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 10922-10926
- Miyauchi, Y.¹ Kobayashi, M.² Tanaka, K.³

54
- 84859575409
- Minami, Y.; Shiraishi, Y.; Yamada, K.; Hiyama, T. J. Am. Chem. Soc. 2012, 134, 6124-6127
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 6124-6127
- Minami, Y.¹ Shiraishi, Y.² Yamada, K.³ Hiyama, T.⁴

55
- 84867363774
- Verrier, C.; Carret, S.; Poisson, J. F. Org. Lett. 2012, 14, 5122-5125
- (2012) Org. Lett. , vol.14 , pp. 5122-5125
- Verrier, C.¹ Carret, S.² Poisson, J.F.³

56
- 84885093747
- Cui, W.; Mao, M.; He, Z.; Zhu, G. J. Org. Chem. 2013, 78, 9815-9821
- (2013) J. Org. Chem. , vol.78 , pp. 9815-9821
- Cui, W.¹ Mao, M.² He, Z.³ Zhu, G.⁴

57
- 84884829614
- Minami, Y.; Yamada, K.; Hiyama, T. Angew. Chem., Int. Ed. 2013, 52, 10611-10615
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 10611-10615
- Minami, Y.¹ Yamada, K.² Hiyama, T.³

58
- 54049093686
- Raushel, J.; Pitram, S. M.; Fokin, V. V. Org. Lett. 2008, 10, 3385-3388
- (2008) Org. Lett. , vol.10 , pp. 3385-3388
- Raushel, J.¹ Pitram, S.M.² Fokin, V.V.³

59
- 78049513722
- Raushel, J.; Fokin, V. V. Org. Lett. 2010, 12, 4952-4955
- (2010) Org. Lett. , vol.12 , pp. 4952-4955
- Raushel, J.¹ Fokin, V.V.²

60
- 80052765079
- Zibinsky, M.; Fokin, V. V. Org. Lett. 2011, 13, 4870-4872
- (2011) Org. Lett. , vol.13 , pp. 4870-4872
- Zibinsky, M.¹ Fokin, V.V.²

61
- 80051673452
- Ovalles, S. R.; Hansen, J. H.; Davies, H. M. L. Org. Lett. 2011, 13, 4284-4287
- (2011) Org. Lett. , vol.13 , pp. 4284-4287
- Ovalles, S.R.¹ Hansen, J.H.² Davies, H.M.L.³

62
- 84866036067
- Hansen, S. R.; Spangler, J. E.; Hansen, J. H.; Davies, H. M. L. Org. Lett. 2012, 14, 4626-4629
- (2012) Org. Lett. , vol.14 , pp. 4626
- Hansen, S.R.¹ Spangler, J.E.² Hansen, J.H.³ Davies, H.M.L.⁴

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