SCOPUS 정보 검색 플랫폼

Volumn 51, Issue 35, 2015, Pages 7558-7561

Catalytic asymmetric hydrogenation of quinoline carbocycles: Unusual chemoselectivity in the hydrogenation of quinolines

(3) Kuwano, Ryoichi a,b Ikeda, Ryuhei a Hirasada, Kazuki a

a KYUSHU UNIVERSITY (Japan)

b JAPAN SCIENCE AND TECHNOLOGY AGENCY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5,6,7,8 TETRAHYDROQUINOLINE; DEUTERIUM; PLATINUM; QUINOLINE CARBOCYCLE; QUINOLINE DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; HYDROGENOLYSIS; STEREOCHEMISTRY;

EID: 84928320662 PISSN: 13597345 EISSN: 1364548X Source Type: Journal
DOI: 10.1039/c5cc01971k Document Type: Article

Times cited : (54)

References (62)

1
- 29144521717
- F. Glorius Org. Biomol. Chem. 2005 3 4171
- (2005) Org. Biomol. Chem. , vol.3 , pp. 4171
- Glorius, F.¹

2
- 38049066005
- Y.-G. Zhou Acc. Chem. Res. 2007 40 1357
- (2007) Acc. Chem. Res. , vol.40 , pp. 1357
- Zhou, Y.-G.¹

3
- 61349102524
- R. Kuwano Heterocycles 2008 76 909
- (2008) Heterocycles , vol.76 , pp. 909
- Kuwano, R.¹

4
- 84856417672
- D.-S. Wang Q.-A. Chen S.-M. Lu Y.-G. Zhou Chem. Rev. 2012 112 2557
- (2012) Chem. Rev. , vol.112 , pp. 2557
- Wang, D.-S.¹ Chen, Q.-A.² Lu, S.-M.³ Zhou, Y.-G.⁴

5
- 84883547479
- D. Zhao F. Glorius Angew. Chem., Int. Ed. 2013 52 9616
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 9616
- Zhao, D.¹ Glorius, F.²

6
- 84890912060
- K. Mashima T. Nagano A. Iimuro K. Yamaji Y. Kita Heterocycles 2014 88 103
- (2014) Heterocycles , vol.88 , pp. 103
- Mashima, K.¹ Nagano, T.² Iimuro, A.³ Yamaji, K.⁴ Kita, Y.⁵

7
- 84994449354
- For reports on the asymmetric hydrogenation of o-disubstituted benzenes bearing a chiral auxiliary, see
- L. Shi Z.-S. Ye Y.-G. Zhou Synlett 2014 928
- (2014) Synlett , pp. 928
- Shi, L.¹ Ye, Z.-S.² Zhou, Y.-G.³

8
- 0001134614
- M. Besson B. Blanc M. Champelet P. Gallezot K. Nasar C. Pinel J. Catal. 1997 170 254
- (1997) J. Catal. , vol.170 , pp. 254
- Besson, M.¹ Blanc, B.² Champelet, M.³ Gallezot, P.⁴ Nasar, K.⁵ Pinel, C.⁶

9
- 0002192518
- M. Besson S. Neto C. Pinel Chem. Commun. 1998 1431
- (1998) Chem. Commun. , pp. 1431
- Besson, M.¹ Neto, S.² Pinel, C.³

10
- 0001348845
- V. S. Ranade R. Prins J. Catal. 1999 185 479
- (1999) J. Catal. , vol.185 , pp. 479
- Ranade, V.S.¹ Prins, R.²

11
- 0034677690
- The hydrogenation of benzene rings has been attempted by using ruthenium nanoparticles modified with chiral N-donor ligands
- M. Besson F. Delbecq P. Gallezot S. Neto C. Pinel Chem.-Eur. J. 2000 6 949
- (2000) Chem.-Eur. J. , vol.6 , pp. 949
- Besson, M.¹ Delbecq, F.² Gallezot, P.³ Neto, S.⁴ Pinel, C.⁵

12
- 33645520376
- S. Jansat D. Picurelli K. Pelzer K. Philippot M. Gomez G. Muller P. Lecante B. Chaudret New J. Chem. 2006 30 115
- (2006) New J. Chem. , vol.30 , pp. 115
- Jansat, S.¹ Picurelli, D.² Pelzer, K.³ Philippot, K.⁴ Gomez, M.⁵ Muller, G.⁶ Lecante, P.⁷ Chaudret, B.⁸

13
- 45149110472
- A. Gual M. R. Axet K. Philippot B. Chaudret A. Denicourt-Nowicki A. Roucoux S. Castillon C. Claver Chem. Commun. 2008 2759
- (2008) Chem. Commun. , pp. 2759
- Gual, A.¹ Axet, M.R.² Philippot, K.³ Chaudret, B.⁴ Denicourt-Nowicki, A.⁵ Roucoux, A.⁶ Castillon, S.⁷ Claver, C.⁸

14
- 79953689291
- S. Urban N. Ortega F. Glorius Angew. Chem., Int. Ed. 2011 50 3803
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 3803
- Urban, S.¹ Ortega, N.² Glorius, F.³

15
- 84859941747
- R. Kuwano R. Morioka M. Kashiwabara N. Kameyama Angew. Chem., Int. Ed. 2012 51 4136
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 4136
- Kuwano, R.¹ Morioka, R.² Kashiwabara, M.³ Kameyama, N.⁴

16
- 0000920053
- M. Sawamura H. Hamashima M. Sugawara R. Kuwano Y. Ito Organometallics 1995 14 4549
- (1995) Organometallics , vol.14 , pp. 4549
- Sawamura, M.¹ Hamashima, H.² Sugawara, M.³ Kuwano, R.⁴ Ito, Y.⁵

17
- 35048878895
- ed. S. M. Roberts and J. Whittall, John Wiley & Sons, West Sussex, For representative reports on the iridium-catalyzed asymmetric reduction of quinolines, see
- R. Kuwano and M. Sawamura, in Catalysts for Fine Chemical Synthesis, Volume 5: Regio- and Stereo-Controlled Oxidations and Reductions, ed., S. M. Roberts, and, J. Whittall, John Wiley & Sons, West Sussex, 2007, p. 73
- (2007) Catalysts for Fine Chemical Synthesis, Volume 5: Regio- And Stereo-Controlled Oxidations and Reductions , pp. 73
- Kuwano, R.¹ Sawamura, M.²

18
- 0041825591
- W.-B. Wang S.-M. Lu P.-Y. Yang X.-W. Han Y.-G. Zhou J. Am. Chem. Soc. 2003 125 10536
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 10536
- Wang, W.-B.¹ Lu, S.-M.² Yang, P.-Y.³ Han, X.-W.⁴ Zhou, Y.-G.⁵

19
- 28244476491
- K. H. Lam L. Xu L. Feng Q.-H. Fan F. L. Lam W.-h. Lo A. S. C. Chan Adv. Synth. Catal. 2005 347 1755
- (2005) Adv. Synth. Catal. , vol.347 , pp. 1755
- Lam, K.H.¹ Xu, L.² Feng, L.³ Fan, Q.-H.⁴ Lam, F.L.⁵ Lo, W.-H.⁶ Chan, A.S.C.⁷

20
- 33745576403
- S.-M. Lu Y.-Q. Wang X.-W. Han Y.-G. Zhou Angew. Chem., Int. Ed. 2006 45 2260
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 2260
- Lu, S.-M.¹ Wang, Y.-Q.² Han, X.-W.³ Zhou, Y.-G.⁴

21
- 33744955308
- M. T. Reetz X. Li Chem. Commun. 2006 2159
- (2006) Chem. Commun. , pp. 2159
- Reetz, M.T.¹ Li, X.²

22
- 53849143611
- S.-M. Lu C. Bolm Adv. Synth. Catal. 2008 350 1101
- (2008) Adv. Synth. Catal. , vol.350 , pp. 1101
- Lu, S.-M.¹ Bolm, C.²

23
- 58149202442
- Z.-W. Li T.-L. Wang Y.-M. He Z.-J. Wang Q.-H. Fan J. Pan L.-J. Xu Org. Lett. 2008 10 5265
- (2008) Org. Lett. , vol.10 , pp. 5265
- Li, Z.-W.¹ Wang, T.-L.² He, Y.-M.³ Wang, Z.-J.⁴ Fan, Q.-H.⁵ Pan, J.⁶ Xu, L.-J.⁷

24
- 64549090253
- D.-W. Wang X.-B. Wang D.-S. Wang S.-M. Lu Y.-G. Zhou Y.-X. Li J. Org. Chem. 2009 74 2780
- (2009) J. Org. Chem. , vol.74 , pp. 2780
- Wang, D.-W.¹ Wang, X.-B.² Wang, D.-S.³ Lu, S.-M.⁴ Zhou, Y.-G.⁵ Li, Y.-X.⁶

25
- 77951297663
- D.-S. Wang Y.-G. Zhou Tetrahedron Lett. 2010 51 3014
- (2010) Tetrahedron Lett. , vol.51 , pp. 3014
- Wang, D.-S.¹ Zhou, Y.-G.²

26
- 77954674180
- W. Tang Y. Sun X. Lijin T. Wang F. Qinghua K.-H. Lam A. S. C. Chan Org. Biomol. Chem. 2010 8 3464
- (2010) Org. Biomol. Chem. , vol.8 , pp. 3464
- Tang, W.¹ Sun, Y.² Lijin, X.³ Wang, T.⁴ Qinghua, F.⁵ Lam, K.-H.⁶ Chan, A.S.C.⁷

27
- 78650673887
- J. L. Núñez-Rico H. Fernández-Pérez J. Benet-Buchholz A. Vidal-Ferran Organometallics 2010 29 6627
- (2010) Organometallics , vol.29 , pp. 6627
- Núñez-Rico, J.L.¹ Fernández-Pérez, H.² Benet-Buchholz, J.³ Vidal-Ferran, A.⁴

28
- 78649844949
- M. Rueping R. M. Koenigs Chem. Commun. 2011 47 304
- (2011) Chem. Commun. , vol.47 , pp. 304
- Rueping, M.¹ Koenigs, R.M.²

29
- 84863011611
- Q.-A. Chen K. Gao Y. Duan Z.-S. Ye L. Shi Y. Yang Y.-G. Zhou J. Am. Chem. Soc. 2012 134 2442
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 2442
- Chen, Q.-A.¹ Gao, K.² Duan, Y.³ Ye, Z.-S.⁴ Shi, L.⁵ Yang, Y.⁶ Zhou, Y.-G.⁷

30
- 84900846844
- For the asymmetric reduction of quinolines using metals other than iridium and ruthenium, see
- X.-F. Cai R.-N. Guo M.-W. Chen L. Shi Y.-G. Zhou Chem.-Eur. J. 2014 20 7245
- (2014) Chem.-Eur. J. , vol.20 , pp. 7245
- Cai, X.-F.¹ Guo, R.-N.² Chen, M.-W.³ Shi, L.⁴ Zhou, Y.-G.⁵

31
- 70349902205
- C. Wang C. Li X. Wu A. Pettman J. Xiao Angew. Chem., Int. Ed. 2009 48 6524
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 6524
- Wang, C.¹ Li, C.² Wu, X.³ Pettman, A.⁴ Xiao, J.⁵

32
- 84868098711
- X.-F. Tu L.-Z. Gong Angew. Chem., Int. Ed. 2012 51 11346
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 11346
- Tu, X.-F.¹ Gong, L.-Z.²

33
- 84904999969
- For representative reports on the asymmetric transfer hydrogenation of quinolines through organocatalysis, see
- X.-F. Cai W.-X. Huang Z.-P. Chen Y.-G. Zhou Chem. Commun. 2014 50 9588
- (2014) Chem. Commun. , vol.50 , pp. 9588
- Cai, X.-F.¹ Huang, W.-X.² Chen, Z.-P.³ Zhou, Y.-G.⁴

34
- 33746269442
- M. Rueping A. P. Antonchick T. Theissmann Angew. Chem., Int. Ed. 2006 45 3683
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 3683
- Rueping, M.¹ Antonchick, A.P.² Theissmann, T.³

35
- 38349018738
- Q.-S. Guo D.-M. Du J. Xu Angew. Chem., Int. Ed. 2008 47 759
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 759
- Guo, Q.-S.¹ Du, D.-M.² Xu, J.³

36
- 80052692148
- M. Rueping T. Theissmann M. Stoeckel A. P. Antonchick Org. Biomol. Chem. 2011 9 6844
- (2011) Org. Biomol. Chem. , vol.9 , pp. 6844
- Rueping, M.¹ Theissmann, T.² Stoeckel, M.³ Antonchick, A.P.⁴

37
- 84879462165
- X.-F. Cai M.-W. Chen Z.-S. Ye R.-N. Guo L. Shi Y.-Q. Li Y.-G. Zhou Chem.-Asian J. 2013 8 1381
- (2013) Chem.-Asian J. , vol.8 , pp. 1381
- Cai, X.-F.¹ Chen, M.-W.² Ye, Z.-S.³ Guo, R.-N.⁴ Shi, L.⁵ Li, Y.-Q.⁶ Zhou, Y.-G.⁷

38
- 84900854230
- X.-F. Cai R.-N. Guo G.-S. Feng B. Wu Y.-G. Zhou Org. Lett. 2014 16 2680
- (2014) Org. Lett. , vol.16 , pp. 2680
- Cai, X.-F.¹ Guo, R.-N.² Feng, G.-S.³ Wu, B.⁴ Zhou, Y.-G.⁵

39
- 54249139518
- H. Zhou Z. Li Z. Wang T. Wang L. Xu Y. He Q.-H. Fan J. Pan L. Gu A. S. C. Chan Angew. Chem., Int. Ed. 2008 47 8464
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 8464
- Zhou, H.¹ Li, Z.² Wang, Z.³ Wang, T.⁴ Xu, L.⁵ He, Y.⁶ Fan, Q.-H.⁷ Pan, J.⁸ Gu, L.⁹ Chan, A.S.C.¹⁰

40
- 67649132809
- Z.-J. Wang H.-F. Zhou T.-L. Wang Y.-M. He Q.-H. Fan Green Chem. 2009 11 767
- (2009) Green Chem. , vol.11 , pp. 767
- Wang, Z.-J.¹ Zhou, H.-F.² Wang, T.-L.³ He, Y.-M.⁴ Fan, Q.-H.⁵

41
- 77956650164
- V. Parekh J. A. Ramsden M. Wills Tetrahedron: Asymmetry 2010 21 1549
- (2010) Tetrahedron: Asymmetry , vol.21 , pp. 1549
- Parekh, V.¹ Ramsden, J.A.² Wills, M.³

42
- 79959493473
- T. Wang L.-G. Zhuo Z. Li F. Chen Z. Ding Y. He Q.-H. Fan J. Xiang Z.-X. Yu A. S. C. Chan J. Am. Chem. Soc. 2011 133 9878
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 9878
- Wang, T.¹ Zhuo, L.-G.² Li, Z.³ Chen, F.⁴ Ding, Z.⁵ He, Y.⁶ Fan, Q.-H.⁷ Xiang, J.⁸ Yu, Z.-X.⁹ Chan, A.S.C.¹⁰

43
- 84890786194
- Z.-Y. Ding T. Wang Y.-M. He F. Chen H.-F. Zhou Q.-H. Fan Q. Guo A. S. C. Chan Adv. Synth. Catal. 2013 355 3727
- (2013) Adv. Synth. Catal. , vol.355 , pp. 3727
- Ding, Z.-Y.¹ Wang, T.² He, Y.-M.³ Chen, F.⁴ Zhou, H.-F.⁵ Fan, Q.-H.⁶ Guo, Q.⁷ Chan, A.S.C.⁸

44
- 84905694211
- Z. Yang F. Chen Y.-M. He N. Yang Q.-H. Fan Catal. Sci. Technol. 2014 4 2887
- (2014) Catal. Sci. Technol. , vol.4 , pp. 2887
- Yang, Z.¹ Chen, F.² He, Y.-M.³ Yang, N.⁴ Fan, Q.-H.⁵

45
- 0005102906
- F. W. Vierhapper E. L. Eliel J. Am. Chem. Soc. 1974 96 2256
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 2256
- Vierhapper, F.W.¹ Eliel, E.L.²

46
- 0000049705
- F. W. Vierhapper E. L. Eliel J. Org. Chem. 1975 40 2729
- (1975) J. Org. Chem. , vol.40 , pp. 2729
- Vierhapper, F.W.¹ Eliel, E.L.²

47
- 37049105836
- M. Hönel F. W. Vierhapper J. Chem. Soc., Perkin Trans. 1 1980 1933
- (1980) J. Chem. Soc., Perkin Trans. 1 , pp. 1933
- Hönel, M.¹ Vierhapper, F.W.²

48
- 0020425546
- H. Gildemeister H. Knorr H. Mildenberger G. Salbeck Liebigs Ann. Chem. 1982 1656
- (1982) Liebigs Ann. Chem. , pp. 1656
- Gildemeister, H.¹ Knorr, H.² Mildenberger, H.³ Salbeck, G.⁴

49
- 37049098608
- M. Hönel F. W. Vierhapper J. Chem. Soc., Perkin Trans. 1 1982 2607
- (1982) J. Chem. Soc., Perkin Trans. 1 , pp. 2607
- Hönel, M.¹ Vierhapper, F.W.²

50
- 2142734703
- M. Hönel F. W. Vierhapper Monatsh. Chem. 1984 115 1219
- (1984) Monatsh. Chem. , vol.115 , pp. 1219
- Hönel, M.¹ Vierhapper, F.W.²

51
- 0036828173
- K. A. Skupinska E. J. McEachern R. T. Skerlj G. J. Bridger J. Org. Chem. 2002 67 7890
- (2002) J. Org. Chem. , vol.67 , pp. 7890
- Skupinska, K.A.¹ McEachern, E.J.² Skerlj, R.T.³ Bridger, G.J.⁴

52
- 0141991176
- A. Solladié-Cavallo M. Roje A. Baram V. Šunjić Tetrahedron Lett. 2003 44 8501
- (2003) Tetrahedron Lett. , vol.44 , pp. 8501
- Solladié-Cavallo, A.¹ Roje, M.² Baram, A.³ Šunjić, V.⁴

53
- 0038303167
- A. F. Borowski S. Sabo-Etienne B. Donnadieu B. Chaudret Organometallics 2003 22 1630
- (2003) Organometallics , vol.22 , pp. 1630
- Borowski, A.F.¹ Sabo-Etienne, S.² Donnadieu, B.³ Chaudret, B.⁴

54
- 84868657007
- A. F. Borowski L. Vendier S. Sabo-Etienne E. Rozycka-Sokolowska A. V. Gaudyn Dalton Trans. 2012 41 14117
- (2012) Dalton Trans. , vol.41 , pp. 14117
- Borowski, A.F.¹ Vendier, L.² Sabo-Etienne, S.³ Rozycka-Sokolowska, E.⁴ Gaudyn, A.V.⁵

55
- 77149159726
- M. Heitbaum R. Fröhlich F. Glorius Adv. Synth. Catal. 2010 352 357
- (2010) Adv. Synth. Catal. , vol.352 , pp. 357
- Heitbaum, M.¹ Fröhlich, R.² Glorius, F.³

56
- 33745579608
- R. Kuwano M. Kashiwabara Org. Lett. 2006 8 2653
- (2006) Org. Lett. , vol.8 , pp. 2653
- Kuwano, R.¹ Kashiwabara, M.²

57
- 38349135761
- R. Kuwano M. Kashiwabara M. Ohsumi H. Kusano J. Am. Chem. Soc. 2008 130 808
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 808
- Kuwano, R.¹ Kashiwabara, M.² Ohsumi, M.³ Kusano, H.⁴

58
- 79955897582
- R. Kuwano N. Kameyama R. Ikeda J. Am. Chem. Soc. 2011 133 7312
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 7312
- Kuwano, R.¹ Kameyama, N.² Ikeda, R.³

59
- 0037155540
- See ESI
- T. Rodima I. Kaljurand A. Pihl V. Mäemets I. Leito I. A. Koppel J. Org. Chem. 2002 67 1873
- (2002) J. Org. Chem. , vol.67 , pp. 1873
- Rodima, T.¹ Kaljurand, I.² Pihl, A.³ Mäemets, V.⁴ Leito, I.⁵ Koppel, I.A.⁶

60
- 0001273963
- L.-L. Gundersen T. Benneche K. Undheim J. Legendziewicz P. Kierkegaard Acta Chem. Scand. 1989 43 706
- (1989) Acta Chem. Scand. , vol.43 , pp. 706
- Gundersen, L.-L.¹ Benneche, T.² Undheim, K.³ Legendziewicz, J.⁴ Kierkegaard, P.⁵

61
- 33747233073
- S. Kaiser S. P. Smidt A. Pfaltz Angew. Chem., Int. Ed. 2006 45 5194
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 5194
- Kaiser, S.¹ Smidt, S.P.² Pfaltz, A.³

62
- 0036229349
- J. Uenishi M. Hamada Synthesis 2002 625
- (2002) Synthesis , pp. 625
- Uenishi, J.¹ Hamada, M.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.