SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 55, Issue 16, 2016, Pages 5014-5018

Desilylation-Activated Propargylic Transformation: Enantioselective Copper-Catalyzed [3+2] Cycloaddition of Propargylic Esters with β-Naphthol or Phenol Derivatives

(5) Shao, Long a,b Wang, Ya Hui a Zhang, De Yang a,b Xu, Jie a Hu, Xiang Ping a

a DALIAN INSTITUTE OF CHEMICAL PHYSICS (China)

b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES (China)

Author keywords

asymmetric catalysis; copper; cycloaddition; heterocycles; reaction mechanisms

Indexed keywords

COPPER; CYCLOADDITION; ENANTIOSELECTIVITY; ESTERS; NAPHTHOL; PHENOLS;

2 ,3-DIHYDROBENZOFURANS; ASYMMETRIC CATALYSIS; ASYMMETRIC [3+2] CYCLOADDITION; ELECTRON-RICH PHENOLS; HETEROCYCLES; HIGH ENANTIOSELECTIVITY; REACTION MECHANISM; [3+2]-CYCLOADDITION;

CATALYSIS;

EID: 84960171959 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201510793 Document Type: Article

Times cited : (107)

References (73)

1
- 84962971894
- see
- For reviews, see
- For Reviews

2
- 58249106955
- N. Ljungdahl, N. Kann, Angew. Chem. Int. Ed. 2009, 48, 642;
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 642
- Ljungdahl, N.¹ Kann, N.²

3
- 84960093918
- Angew. Chem. 2009, 121, 652;
- (2009) Angew. Chem. , vol.121 , pp. 652

4
- 77952340938
- Y. Miyake, S. Uemura, Y. Nishibayashi, ChemCatChem 2009, 1, 342;
- (2009) ChemCatChem , vol.1 , pp. 342
- Miyake, Y.¹ Uemura, S.² Nishibayashi, Y.³

5
- 71849098652
- R. J. Detz, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2009, 6263;
- (2009) Eur. J. Org. Chem. , pp. 6263
- Detz, R.J.¹ Hiemstra, H.² Van Maarseveen, J.H.³

6
- 79952664793
- C.-H. Ding, X.-L. Hou, Chem. Rev. 2011, 111, 1914;
- (2011) Chem. Rev. , vol.111 , pp. 1914
- Ding, C.-H.¹ Hou, X.-L.²

7
- 84857033087
- Y. Nishibayashi, Synthesis 2012, 489;
- (2012) Synthesis , pp. 489
- Nishibayashi, Y.¹

8
- 84858738346
- E. B. Bauer, Synthesis 2012, 1131;
- (2012) Synthesis , pp. 1131
- Bauer, E.B.¹

9
- 84949115391
- D.-Y. Zhang, X.-P. Hu, Tetrahedron Lett. 2015, 56, 283.
- (2015) Tetrahedron Lett. , vol.56 , pp. 283
- Zhang, D.-Y.¹ Hu, X.-P.²

10
- 28744444549
- Y. Inada, Y. Nishibayashi, S. Uemura, Angew. Chem. Int. Ed. 2005, 44, 7715;
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 7715
- Inada, Y.¹ Nishibayashi, Y.² Uemura, S.³

11
- 33746789659
- Angew. Chem. 2005, 117, 7893;
- (2005) Angew. Chem. , vol.117 , pp. 7893

12
- 34548303280
- H. Matsuzawa, Y. Miyake, Y. Nishibayashi, Angew. Chem. Int. Ed. 2007, 46, 6488;
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 6488
- Matsuzawa, H.¹ Miyake, Y.² Nishibayashi, Y.³

13
- 53549132597
- Angew. Chem. 2007, 119, 6608;
- (2007) Angew. Chem. , vol.119 , pp. 6608

14
- 38349176541
- H. Matsuzawa, K. Kanao, Y. Miyake, Y. Nishibayashi, Org. Lett. 2007, 9, 5561;
- (2007) Org. Lett. , vol.9 , pp. 5561
- Matsuzawa, H.¹ Kanao, K.² Miyake, Y.³ Nishibayashi, Y.⁴

15
- 49449095350
- K. Fukamizu, Y. Miyake, Y. Nishibayashi, J. Am. Chem. Soc. 2008, 130, 10498;
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 10498
- Fukamizu, K.¹ Miyake, Y.² Nishibayashi, Y.³

16
- 66149086459
- K. Kanao, Y. Miyake, Y. Nishibayashi, Organometallics 2009, 28, 2920;
- (2009) Organometallics , vol.28 , pp. 2920
- Kanao, K.¹ Miyake, Y.² Nishibayashi, Y.³

17
- 77956915666
- M. Ikeda, Y. Miyake, Y. Nishibayashi, Angew. Chem. Int. Ed. 2010, 49, 7289;
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 7289
- Ikeda, M.¹ Miyake, Y.² Nishibayashi, Y.³

18
- 79952046183
- Angew. Chem. 2010, 122, 7447;
- (2010) Angew. Chem. , vol.122 , pp. 7447

19
- 84857031592
- M. Ikeda, Y. Miyake, Y. Nishibayashi, Chem. Eur. J. 2012, 18, 3321;
- (2012) Chem. Eur. J. , vol.18 , pp. 3321
- Ikeda, M.¹ Miyake, Y.² Nishibayashi, Y.³

20
- 84861142879
- M. Ikeda, Y. Miyake, Y. Nishibayashi, Organometallics 2012, 31, 3810;
- (2012) Organometallics , vol.31 , pp. 3810
- Ikeda, M.¹ Miyake, Y.² Nishibayashi, Y.³

21
- 85027937812
- Y. Senda, K. Nakajima, Y. Nishibayashi, Angew. Chem. Int. Ed. 2015, 54, 4060;
- (2015) Angew. Chem. Int. Ed. , vol.54 , pp. 4060
- Senda, Y.¹ Nakajima, K.² Nishibayashi, Y.³

22
- 84960133833
- Angew. Chem. 2015, 127, 4132.
- (2015) Angew. Chem. , vol.127 , pp. 4132

23
- 84962940613
- see
- For enantioselective copper-catalyzed propargylic transformation, see
- For Enantioselective Copper-catalyzed Propargylic Transformation

24
- 45549088523
- R. J. Detz, M. M. E. Delville, H. Hiemstra, J. H. van Maarseveen, Angew. Chem. Int. Ed. 2008, 47, 3777;
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3777
- Detz, R.J.¹ Delville, M.M.E.² Hiemstra, H.³ Van Maarseveen, J.H.⁴

25
- 84899488825
- Angew. Chem. 2008, 120, 3837;
- (2008) Angew. Chem. , vol.120 , pp. 3837

26
- 50549097989
- G. Hattori, H. Matsuzawa, Y. Miyake, Y. Nishibayashi, Angew. Chem. Int. Ed. 2008, 47, 3781;
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3781
- Hattori, G.¹ Matsuzawa, H.² Miyake, Y.³ Nishibayashi, Y.⁴

27
- 84899483810
- Angew. Chem. 2008, 120, 3841;
- (2008) Angew. Chem. , vol.120 , pp. 3841

28
- 70349906446
- P. Fang, X.-L. Hou, Org. Lett. 2009, 11, 4612;
- (2009) Org. Lett. , vol.11 , pp. 4612
- Fang, P.¹ Hou, X.-L.²

29
- 70349847238
- G. Hattori, A. Yoshida, Y. Miyake, Y. Nishibayashi, J. Org. Chem. 2009, 74, 7603;
- (2009) J. Org. Chem. , vol.74 , pp. 7603
- Hattori, G.¹ Yoshida, A.² Miyake, Y.³ Nishibayashi, Y.⁴

30
- 77952324547
- G. Hattori, Y. Miyake, Y. Nishibayashi, ChemCatChem 2010, 2, 155;
- (2010) ChemCatChem , vol.2 , pp. 155
- Hattori, G.¹ Miyake, Y.² Nishibayashi, Y.³

31
- 77955025634
- G. Hattori, K. Sakata, H. Matsuzawa, Y. Tanabe, Y. Miyake, Y. Nishibayashi, J. Am. Chem. Soc. 2010, 132, 10592;
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 10592
- Hattori, G.¹ Sakata, K.² Matsuzawa, H.³ Tanabe, Y.⁴ Miyake, Y.⁵ Nishibayashi, Y.⁶

32
- 79955771768
- R. J. Detz, Z. Abiri, R. le Griel, H. Hiemstra, J. H. van Maarseveen, Chem. Eur. J. 2011, 17, 5921;
- (2011) Chem. Eur. J. , vol.17 , pp. 5921
- Detz, R.J.¹ Abiri, Z.² Le Griel, R.³ Hiemstra, H.⁴ Van Maarseveen, J.H.⁵

33
- 79955619524
- A. Yoshida, G. Hattori, Y. Miyake, Y. Nishibayashi, Org. Lett. 2011, 13, 2460;
- (2011) Org. Lett. , vol.13 , pp. 2460
- Yoshida, A.¹ Hattori, G.² Miyake, Y.³ Nishibayashi, Y.⁴

34
- 84869054530
- C. Zhang, Y.-H. Wang, X.-H. Hu, Z. Zheng, J. Xu, X.-P. Hu, Adv. Synth. Catal. 2012, 354, 2854;
- (2012) Adv. Synth. Catal. , vol.354 , pp. 2854
- Zhang, C.¹ Wang, Y.-H.² Hu, X.-H.³ Zheng, Z.⁴ Xu, J.⁵ Hu, X.-P.⁶

35
- 84862224599
- C. Zhang, X.-H. Hu, Y.-H. Wang, Z. Zheng, J. Xu, X.-P. Hu, J. Am. Chem. Soc. 2012, 134, 9585;
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 9585
- Zhang, C.¹ Hu, X.-H.² Wang, Y.-H.³ Zheng, Z.⁴ Xu, J.⁵ Hu, X.-P.⁶

36
- 84887998887
- T. Mino, H. Taguchi, M. Hashimoto, M. Sakamoto, Tetrahedron: Asymmetry 2013, 24, 1520;
- (2013) Tetrahedron: Asymmetry , vol.24 , pp. 1520
- Mino, T.¹ Taguchi, H.² Hashimoto, M.³ Sakamoto, M.⁴

37
- 84893949433
- F.-L. Zhu, Y. Zou, D.-Y. Zhang, Y.-H. Wang, X.-H. Hu, S. Chen, J. Xu, X.-P. Hu, Angew. Chem. Int. Ed. 2014, 53, 1410;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 1410
- Zhu, F.-L.¹ Zou, Y.² Zhang, D.-Y.³ Wang, Y.-H.⁴ Hu, X.-H.⁵ Chen, S.⁶ Xu, J.⁷ Hu, X.-P.⁸

38
- 84982776532
- Angew. Chem. 2014, 126, 1434;
- (2014) Angew. Chem. , vol.126 , pp. 1434

39
- 84896693703
- F.-Z. Han, F.-L. Zhu, Y.-H. Wang, Y. Zou, X.-H. Hu, S. Chen, X.-P. Hu, Org. Lett. 2014, 16, 588;
- (2014) Org. Lett. , vol.16 , pp. 588
- Han, F.-Z.¹ Zhu, F.-L.² Wang, Y.-H.³ Zou, Y.⁴ Hu, X.-H.⁵ Chen, S.⁶ Hu, X.-P.⁷

40
- 84896086242
- Y. Zou, F.-L. Zhu, Z.-C. Duan, Y.-H. Wang, D.-Y. Zhang, Z. Cao, Z. Zheng, X.-P. Hu, Tetrahedron Lett. 2014, 55, 2033;
- (2014) Tetrahedron Lett. , vol.55 , pp. 2033
- Zou, Y.¹ Zhu, F.-L.² Duan, Z.-C.³ Wang, Y.-H.⁴ Zhang, D.-Y.⁵ Cao, Z.⁶ Zheng, Z.⁷ Hu, X.-P.⁸

41
- 84903189573
- M. Shibata, K. Nakajima, Y. Nishibayashi, Chem. Commun. 2014, 50, 7874;
- (2014) Chem. Commun. , vol.50 , pp. 7874
- Shibata, M.¹ Nakajima, K.² Nishibayashi, Y.³

42
- 84910020188
- L. Zhao, G.-X. Huang, B.-B. Guo, L.-J. Xu, J. Chen, W.-G. Cao, G. Zhao, X.-Y. Wu, Org. Lett. 2014, 16, 5584;
- (2014) Org. Lett. , vol.16 , pp. 5584
- Zhao, L.¹ Huang, G.-X.² Guo, B.-B.³ Xu, L.-J.⁴ Chen, J.⁵ Cao, W.-G.⁶ Zhao, G.⁷ Wu, X.-Y.⁸

43
- 84908428680
- B. Wang, C. Liu, H. Guo, RSC Adv. 2014, 4, 53216;
- (2014) RSC Adv. , vol.4 , pp. 53216
- Wang, B.¹ Liu, C.² Guo, H.³

44
- 84908384032
- D.-Y. Zhang, F.-L. Zhu, Y.-H. Wang, X.-H. Hu, S. Chen, C.-J. Hou, X.-P. Hu, Chem. Commun. 2014, 50, 14459;
- (2014) Chem. Commun. , vol.50 , pp. 14459
- Zhang, D.-Y.¹ Zhu, F.-L.² Wang, Y.-H.³ Hu, X.-H.⁴ Chen, S.⁵ Hou, C.-J.⁶ Hu, X.-P.⁷

45
- 84907880290
- F.-L. Zhu, Y.-H. Wang, D.-Y. Zhang, X.-H. Hu, S. Chen, C.-J. Hou, J. Xu, X.-P. Hu, Adv. Synth. Catal. 2014, 356, 3231;
- (2014) Adv. Synth. Catal. , vol.356 , pp. 3231
- Zhu, F.-L.¹ Wang, Y.-H.² Zhang, D.-Y.³ Hu, X.-H.⁴ Chen, S.⁵ Hou, C.-J.⁶ Xu, J.⁷ Hu, X.-P.⁸

46
- 84929611914
- F. Zhu, X. Hu, Chin. J. Catal. 2015, 36, 86;
- (2015) Chin. J. Catal. , vol.36 , pp. 86
- Zhu, F.¹ Hu, X.²

47
- 84941031493
- D.-Y. Zhang, L. Shao, J. Xu, X.-P. Hu, ACS Catal. 2015, 5, 5026;
- (2015) ACS Catal. , vol.5 , pp. 5026
- Zhang, D.-Y.¹ Shao, L.² Xu, J.³ Hu, X.-P.⁴

48
- 84923630644
- K. Nakajima, M. Shibata, Y. Nishibayashi, J. Am. Chem. Soc. 2015, 137, 2472;
- (2015) J. Am. Chem. Soc. , vol.137 , pp. 2472
- Nakajima, K.¹ Shibata, M.² Nishibayashi, Y.³

49
- 84935869255
- W. Shao, H. Li, C. Liu, C.-J. Liu, S.-L. You, Angew. Chem. Int. Ed. 2015, 54, 7684;
- (2015) Angew. Chem. Int. Ed. , vol.54 , pp. 7684
- Shao, W.¹ Li, H.² Liu, C.³ Liu, C.-J.⁴ You, S.-L.⁵

50
- 84977928714
- Angew. Chem. 2015, 127, 7794;
- (2015) Angew. Chem. , vol.127 , pp. 7794

51
- 84942847451
- G. Huang, C. Cheng, L. Ge, B. Guo, L. Zhao, X. Wu, Org. Lett. 2015, 17, 4894.
- (2015) Org. Lett. , vol.17 , pp. 4894
- Huang, G.¹ Cheng, C.² Ge, L.³ Guo, B.⁴ Zhao, L.⁵ Wu, X.⁶

52
- 79959445802
- For other catalytic propargylic transformations, see.
- For other catalytic propargylic transformations, see:, R. Sinisi, M. V. Vita, A. Gualandi, E. Emer, P. G. Cozzi, Chem. Eur. J. 2011, 17, 7404.
- (2011) Chem. Eur. J. , vol.17 , pp. 7404
- Sinisi, R.¹ Vita, M.V.² Gualandi, A.³ Emer, E.⁴ Cozzi, P.G.⁵

53
- 84908064850
- F.-L. Zhu, Y.-H. Wang, D.-Y. Zhang, J. Xu, X.-P. Hu, Angew. Chem. Int. Ed. 2014, 53, 10223;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 10223
- Zhu, F.-L.¹ Wang, Y.-H.² Zhang, D.-Y.³ Xu, J.⁴ Hu, X.-P.⁵

54
- 84926618910
- Angew. Chem. 2014, 126, 10387.
- (2014) Angew. Chem. , vol.126 , pp. 10387

55
- 84949115770
- X.-H. Hu, Z.-T. Liu, L. Shao, X.-P. Hu, Synthesis 2015, 913.
- (2015) Synthesis , pp. 913
- Hu, X.-H.¹ Liu, Z.-T.² Shao, L.³ Hu, X.-P.⁴

56
- 0037055054
- Y. Nishibayashi, Y. Inada, M. Hidai, S. Uemura, J. Am. Chem. Soc. 2002, 124, 7900;
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 7900
- Nishibayashi, Y.¹ Inada, Y.² Hidai, M.³ Uemura, S.⁴

57
- 77951853107
- K. Kanao, Y. Miyake, Y. Nishibayashi, Organometallics 2010, 29, 2126.
- (2010) Organometallics , vol.29 , pp. 2126
- Kanao, K.¹ Miyake, Y.² Nishibayashi, Y.³

58
- 0003607021
- Eds.: A. R. Katrizky, C. W. Rees, Pergamon, Oxford
- D. M. X. Donnelly, M. J. Meegan, in Comprehensive Heterocyclic Chemistry, Vol. 4 (Eds.:, A. R. Katrizky, C. W. Rees,), Pergamon, Oxford, 1984;
- (1984) Comprehensive Heterocyclic Chemistry, Vol. 4
- Donnelly, D.M.X.¹ Meegan, M.J.²

59
- 0035857466
- P. K. Frederiksen, M. Jorgensen, P. R. Ogilby, J. Am. Chem. Soc. 2001, 123, 1215;
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 1215
- Frederiksen, P.K.¹ Jorgensen, M.² Ogilby, P.R.³

60
- 1342307383
- K. K. Park, S.-H. Kim, J. W. Park, J. Photochem. Photobiol. A 2004, 163, 241;
- (2004) J. Photochem. Photobiol. A , vol.163 , pp. 241
- Park, K.K.¹ Kim, S.-H.² Park, J.W.³

61
- 84862909075
- X.-F. Hou, S. Yao, A. Mándi, T. Kurtán, C.-P. Tang, C.-Q. Ke, X.-Q. Li, Y. Ye, Org. Lett. 2012, 14, 460.
- (2012) Org. Lett. , vol.14 , pp. 460
- Hou, X.-F.¹ Yao, S.² Mándi, A.³ Kurtán, T.⁴ Tang, C.-P.⁵ Ke, C.-Q.⁶ Li, X.-Q.⁷ Ye, Y.⁸

62
- 84255162403
- Ł. Albrecht, L. K. Ransborg, V. Lauridsen, M. Overgaard, T. ZweifeL K. A. Jørgensen, Angew. Chem. Int. Ed. 2011, 50, 12496;
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 12496
- Albrecht, Ł.¹ Ransborg, L.K.² Lauridsen, V.³ Overgaard, M.⁴ Jørgensen, T.Z.K.A.⁵

63
- 84866433248
- Angew. Chem. 2011, 123, 12704;
- (2011) Angew. Chem. , vol.123 , pp. 12704

64
- 84873628658
- C. Jarava-Barrera, F. Esteban, C. Navarro-Ranninger, A. Parra, J. Alemán, Chem. Commun. 2013, 49, 2001;
- (2013) Chem. Commun. , vol.49 , pp. 2001
- Jarava-Barrera, C.¹ Esteban, F.² Navarro-Ranninger, C.³ Parra, A.⁴ Alemán, J.⁵

65
- 84887765660
- J.-Y. Pan, X.-S. Li, D.-C. Xu, J.-W. Xie, Aust. J. Chem. 2013, 66, 1415.
- (2013) Aust. J. Chem. , vol.66 , pp. 1415
- Pan, J.-Y.¹ Li, X.-S.² Xu, D.-C.³ Xie, J.-W.⁴

66
- 0030990486
- H. Ito, K. Arimoto, H. Sensul, A. Hosomi, Tetrahedron Lett. 1997, 38, 3977;
- (1997) Tetrahedron Lett. , vol.38 , pp. 3977
- Ito, H.¹ Arimoto, K.² Sensul, H.³ Hosomi, A.⁴

67
- 0034708636
- Y. Nishihara, K. Ikegashira, K. Hirabayashi, J. Ando, A. Mori, T. Hiyama, J. Org. Chem. 2000, 65, 1780;
- (2000) J. Org. Chem. , vol.65 , pp. 1780
- Nishihara, Y.¹ Ikegashira, K.² Hirabayashi, K.³ Ando, J.⁴ Mori, A.⁵ Hiyama, T.⁶

68
- 0005386192
- Y. Nishihara, M. Takemura, A. Mori, K. Osakada, J. Organomet. Chem. 2001, 620, 282;
- (2001) J. Organomet. Chem. , vol.620 , pp. 282
- Nishihara, Y.¹ Takemura, M.² Mori, A.³ Osakada, K.⁴

69
- 57649134973
- Y. Nishihara, E. Inoue, Y. Okada, K. Takagi, Synlett 2008, 3041.
- (2008) Synlett , pp. 3041
- Nishihara, Y.¹ Inoue, E.² Okada, Y.³ Takagi, K.⁴

70
- 14844291349
- R. Shintani, K. Okamoto, T. Hayashi, J. Am. Chem. Soc. 2005, 127, 2872;
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 2872
- Shintani, R.¹ Okamoto, K.² Hayashi, T.³

71
- 60849118120
- Y. Pan, S. Zhao, W. Ji, Z. Zhan, J. Comb. Chem. 2009, 11, 103;
- (2009) J. Comb. Chem. , vol.11 , pp. 103
- Pan, Y.¹ Zhao, S.² Ji, W.³ Zhan, Z.⁴

72
- 84861153820
- For selected example for silyl substituted vinylidene complexes, see
- L. Hao, F. Wu, Z.-C. Ding, S.-X. Xu, Y.-L. Ma, L. Chen, Z.-P. Zhan, Chem. Eur. J. 2012, 18, 6453. For selected example for silyl substituted vinylidene complexes, see
- (2012) Chem. Eur. J. , vol.18 , pp. 6453
- Hao, L.¹ Wu, F.² Ding, Z.-C.³ Xu, S.-X.⁴ Ma, Y.-L.⁵ Chen, L.⁶ Zhan, Z.-P.⁷

73
- 33646058040
- M. Movassaghi, M. D. Hill, J. Am. Chem. Soc. 2006, 128, 4592.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 4592
- Movassaghi, M.¹ Hill, M.D.²

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