SCOPUS 정보 검색 플랫폼

Volumn 19, Issue 42, 2013, Pages 14187-14193

Cooperative catalysis: Combining an achiral metal catalyst with a chiral Brønsted acid enables highly enantioselective hydrogenation of imines

(6) Tang, Weijun a Johnston, Steven a Li, Chaoqun a Iggo, Jonathan A a Bacsa, John a Xiao, Jianliang a

a UNIVERSITY OF LIVERPOOL (United Kingdom)

Author keywords

Asymmetric hydrogenation; Br nsted acid; Cooperative catalysis; Imines; Iridium

Indexed keywords

AMINES; CATALYSIS; CATALYST DEACTIVATION; HYDROGENATION; IRIDIUM; IRIDIUM COMPOUNDS; KETONES; LIGANDS; PHOSPHORIC ACID; REACTION RATES; STEREOCHEMISTRY;

ASYMMETRIC HYDROGENATION; CHEMICAL PRODUCTS; COOPERATIVE CATALYSIS; DIAMINE LIGANDS; ENANTIOSELECTION; ENANTIOSELECTIVE HYDROGENATION; IMINES; STRUCTURAL UNIT;

ENANTIOSELECTIVITY;

EID: 84885591040 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201302437 Document Type: Article

Times cited : (30)

References (71)

1
- 77950345610
- For recent reviews of the asymmetric hydrogenation of imines, see: a) T C. Nugent, M. El-Shazly, Adv. Synth. Catal. 2010, 352, 753-819.
- (2010) Adv. Synth. Catal. , vol.352 , pp. 753-819
- Nugent, T.C.¹ El-Shazly, M.²

2
- 79952684475
- J. H. Xie, S. F Zhu, Q. L. Zhou, Chem. Rev. 2011, 111, 1713-1760;
- (2011) Chem. Rev. , vol.111 , pp. 1713-1760
- Xie, J.H.¹ Zhu, S.F.² Zhou, Q.L.³

3
- 0002164532
- for a significant industrial application, see: c) H.-U Blaser, Adv. Synth. Catal. 2002, 344, 17-31.
- (2002) Adv. Synth. Catal. , vol.344 , pp. 17-31
- Blaser, H.-U.¹

4
- 67650532877
- For recent examples of the asymmetric hydrogenation of imines, see: a) N Mrsic, A.J. Minnaard, B. L. Feringa, J. G. De Vries, J. Am. Chem. Soc. 2009, 131, 8358-8359.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 8358-8359
- Mrsic, N.¹ Minnaard, A.J.² Feringa, B.L.³ De Vries, J.G.⁴

5
- 61849084249
- S. Shirai, H. Nara, Y. Kayaki T. Ikariya Organometallics 2009 28 802-809.
- (2009) Organometallics , vol.28 , pp. 802-809
- Shirai, S.¹ Nara, H.² Kayaki, Y.³ Ikariya, T.⁴

6
- 80051746058
- S. L. Zhou S. Fleischer K. Junge M. Beller Angew. Chem. 2011 123 5226-5230.
- (2011) Angew. Chem. , vol.123 , pp. 5226-5230
- Zhou, S.L.¹ Fleischer, S.² Junge, K.³ Beller, M.⁴

7
- 79956133790
- Angew. Chem. Int. Ed. 2011, 50, 5120-5124.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 5120-5124

8
- 78751606820
- F. Chen, T. L. Wang, Y. M. He, Z. Y. Ding, Z. W. Li, L. J. Xu, Q. H. Fan, Chem. Eur. J. 2011, 17, 1109-1113;
- (2011) Chem. Eur. J. , vol.17 , pp. 1109-1113
- Chen, F.¹ Wang, T.L.² He, Y.M.³ Ding, Z.Y.⁴ Li, Z.W.⁵ Xu, L.J.⁶ Fan, Q.H.⁷

9
- 79251475901
- X. Y Zhou, M. Bao, Y. G. Zhou, Adv. Synth. Catal. 2011, 353, 84-88.
- (2011) Adv. Synth. Catal. , vol.353 , pp. 84-88
- Zhou, X.Y.¹ Bao, M.² Zhou, Y.G.³

10
- 84861685467
- F. Chen, Z. Y. Ding, Y. M. He, J. Qin, T. L. Wang, Q. H. Fan, Tetrahedron 2012, 68, 5248-5257.
- (2012) Tetrahedron , vol.68 , pp. 5248-5257
- Chen, F.¹ Ding, Z.Y.² He, Y.M.³ Qin, J.⁴ Wang, T.L.⁵ Fan, Q.H.⁶

11
- 84863617182
- C. J. Hou, Y. H. Wang, Z. Zheng, J. Xu, X. P. Hu, Org. Lett. 2012, 14, 3554-3557.
- (2012) Org. Lett. , vol.14 , pp. 3554-3557
- Hou, C.J.¹ Wang, Y.H.² Zheng, Z.³ Xu, J.⁴ Hu, X.P.⁵

12
- 84865040314
- N. Arai, N. Utsumi, Y. Matsumoto, K. Murata, K. Tsutsumi, T. Ohkuma, Adv. Synth. Catal. 2012, 354, 2089-2095.
- (2012) Adv. Synth. Catal. , vol.354 , pp. 2089-2095
- Arai, N.¹ Utsumi, N.² Matsumoto, Y.³ Murata, K.⁴ Tsutsumi, K.⁵ Ohkuma, T.⁶

13
- 84867471852
- S. Werkmeister, S. Fleischer, K. Junge, M. Beller, Chem. Asian J. 2012, 7, 2562-2568.
- (2012) Chem. Asian J. , vol.7 , pp. 2562-2568
- Werkmeister, S.¹ Fleischer, S.² Junge, K.³ Beller, M.⁴

14
- 84864590129
- K. Gao, B. Wu, C.B. Yu, Q. A. Chen, Z. S. Ye, Y. G. Zhou, Org. Lett. 2012, 14, 3890-3893.
- (2012) Org. Lett. , vol.14 , pp. 3890-3893
- Gao, K.¹ Wu, B.² Yu, C.B.³ Chen, Q.A.⁴ Ye, Z.S.⁵ Zhou, Y.G.⁶

15
- 84878811190
- Y. Schramm, F. Barrios-Landeros, A. Pfaltz, Chem. Sci. 2013, 4, 2760-2766.
- (2013) Chem. Sci. , vol.4 , pp. 2760-2766
- Schramm, Y.¹ Barrios-Landeros, F.² Pfaltz, A.³

16
- 65549148598
- For selected examples of the metal-catalysed transfer hydrogenation of imines, see: a) H. Matsunaga, K. Nakanishi, M. Nakajima, T. Kunieda, T. Ishizuka, Heterocycles 2009, 78, 617-622.
- (2009) Heterocycles , vol.78 , pp. 617-622
- Matsunaga, H.¹ Nakanishi, K.² Nakajima, M.³ Kunieda, T.⁴ Ishizuka, T.⁵

17
- 68049084689
- D. Guijarro, O. Pablo, M. Yus, Tetrahedron Lett. 2009, 50, 5386-5388.
- (2009) Tetrahedron Lett. , vol.50 , pp. 5386-5388
- Guijarro, D.¹ Pablo, O.² Yus, M.³

18
- 77955169176
- D. Guijarro, O. Pablo, M. Yus, J. Org. Chem. 2010, 75, 5265-5270.
- (2010) J. Org. Chem. , vol.75 , pp. 5265-5270
- Guijarro, D.¹ Pablo, O.² Yus, M.³

19
- 77956494600
- S. H. Kwak, S. A. Lee, K. I. Lee, Tetrahedron: Asymmetry 2010, 21, 800-804.
- (2010) Tetrahedron: Asymmetry , vol.21 , pp. 800-804
- Kwak, S.H.¹ Lee, S.A.² Lee, K.I.³

20
- 84866006596
- A. A. Mikhailine, M. I. Maishan, R. H. Morris, Org. Lett. 2012, 14, 4638-4641.
- (2012) Org. Lett. , vol.14 , pp. 4638-4641
- Mikhailine, A.A.¹ Maishan, M.I.² Morris, R.H.³

21
- 84866130479
- P. Sot, M. Kuzma, J. Václarfk, J. Penchácěk, J. Prěch, J. Januščák, P. Kacer, Organometallics 2012, 31, 6496-6499.
- (2012) Organometallics , vol.31 , pp. 6496-6499
- Sot, P.¹ Kuzma, M.² Václarfk, J.³ Penchácěk, J.⁴ Prěch, J.⁵ Januščák, J.⁶ Kacer, P.⁷

22
- 77950248809
- For recent reviews of the organocatalytic transfer hydrogenation of imines, see: a) D. Kampen, C. M. Reisinger, B. J. List, Top. Curr. Chem. 2009, 291, 395-456.
- (2009) Top. Curr. Chem. , vol.291 , pp. 395-456
- Kampen, D.¹ Reisinger, C.M.² List, B.J.³

23
- 77955689770
- Z. Wang, Z. Jiang, Asian J. Chem. 2010, 22, 4141-4149.
- (2010) Asian J. Chem. , vol.22 , pp. 4141-4149
- Wang, Z.¹ Jiang, Z.²

24
- 77949893012
- M. Rueping, E. Sugiono, F R. Schoepke, Synlett 2010, 852-865.
- (2010) Synlett , pp. 852-865
- Rueping, M.¹ Sugiono, E.² Schoepke, F.R.³

25
- 84857592302
- C. Zheng, S. L. You, Chem. Soc. Rev. 2012, 41, 2498-2518.
- (2012) Chem. Soc. Rev. , vol.41 , pp. 2498-2518
- Zheng, C.¹ You, S.L.²

26
- 79960832378
- J. G. De Vries, N. Mrsic, Catal. Sci. Technol. 2011, 1, 727-735.
- (2011) Catal. Sci. Technol. , vol.1 , pp. 727-735
- De Vries, J.G.¹ Mrsic, N.²

27
- 84857519105
- For a recent review of the asymmetric hydrosilylation of imines, see: S. Jones, C. J. A. Warner, Org. Biomol. Chem. 2012, 10, 2189-2200.
- (2012) Org. Biomol. Chem. , vol.10 , pp. 2189-2200
- Jones, S.¹ Warner, C.J.A.²

28
- 35648936955
- (Eds.: J. G. de Vries, C. J. Elsevier), Wiley-VCH, Weinheim
- F. Spinder, H.-U. Blaser in Handbook of Homogeneous Hydrogenation (Eds.: J. G. de Vries, C. J. Elsevier), Wiley-VCH, Weinheim, 2007, p. 1193.
- (2007) Handbook of Homogeneous Hydrogenation , pp. 1193
- Spinder, F.¹ Blaser, H.-U.²

29
- 3242688725
- M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keßeler, R. Stuürmer, T. Zelinski, Angew. Chem. 2004, 116, 806-843.
- (2004) Angew. Chem. , vol.116 , pp. 806-843
- Breuer, M.¹ Ditrich, K.² Habicher, T.³ Hauer, B.⁴ Keßeler, M.⁵ Stuürmer, R.⁶ Zelinski, T.⁷

30
- 1842578074
- Angew. Chem. Int. Ed. 2004, 43, 788-824.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 788-824

31
- 0003445429
- (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin
- For reviews, see: a) Comprehensive Asymmetric Catalysis, Vols. I-III (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin, 1999.
- (1999) Comprehensive Asymmetric Catalysis , vol.1-3

32
- 84890970875
- Wiley-VCH, Weinheim
- Modern Reduction Methods (Eds.: P. G. Andersson, I. J. Munslow), Wiley-VCH, Weinheim, 2008.
- (2008) Modern Reduction Methods
- Andersson, P.G.¹ Munslow, I.J.²

33
- 61449196772
- L. Rubio-Pérez, F J. Perez-Flores, P. Sharma, L. Velaso, A. Cabrera, Org. Lett. 2009, 11, 265-268.
- (2009) Org. Lett. , vol.11 , pp. 265-268
- Rubio-Pérez, L.¹ Perez-Flores, F.J.² Sharma, P.³ Velaso, L.⁴ Cabrera, A.⁵

34
- 55549096408
- C. Q. Li, C. Wang, B. Villa-Marcos, J. L. Xiao, J. Am. Chem. Soc. 2008, 130, 14450-14451.
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14450-14451
- Li, C.Q.¹ Wang, C.² Villa-Marcos, B.³ Xiao, J.L.⁴

35
- 70349140575
- C. Q. Li, B. Villa-Marcos, J.L. Xiao, J. Am. Chem. Soc. 2009, 131, 6967-6969.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 6967-6969
- Li, C.Q.¹ Villa-Marcos, B.² Xiao, J.L.³

36
- 77951870308
- B. Villa-Marcos, C. Q. Li, K. R. Mulholland, P. J. Hogan, J. L. Xiao, Molecules 2010, 15, 2453-2472.
- (2010) Molecules , vol.15 , pp. 2453-2472
- Villa-Marcos, B.¹ Li, C.Q.² Mulholland, K.R.³ Hogan, P.J.⁴ Xiao, J.L.⁵

37
- 70349943846
- For reviews, see: a) Z. H. Shao, H. B. Zhang, Chem. Soc. Rev. 2009, 38, 2745-2755.
- (2009) Chem. Soc. Rev. , vol.38 , pp. 2745-2755
- Shao, Z.H.¹ Zhang, H.B.²

38
- 77952637874
- C. Zhong, X. Shi, Eur. J. Org. Chem. 2010, 2999-3025.
- (2010) Eur. J. Org. Chem. , pp. 2999-3025
- Zhong, C.¹ Shi, X.²

39
- 77955808773
- M. Rueping, R. M. Koenigs, J. Atodiresei, Chem. Eur. J. 2010, 16, 9350-9365.
- (2010) Chem. Eur. J. , vol.16 , pp. 9350-9365
- Rueping, M.¹ Koenigs, R.M.² Atodiresei, J.³

40
- 84857350578
- A. E. Allen, D. W. C. MacMillan, Chem. Sci. 2012, 3, 633-658.
- (2012) Chem. Sci. , vol.3 , pp. 633-658
- Allen, A.E.¹ MacMillan, D.W.C.²

41
- 84858018586
- L. Stegbauer, F. Sladojevich, D. J. Dixon, Chem. Sci. 2012, 3, 942-958.
- (2012) Chem. Sci. , vol.3 , pp. 942-958
- Stegbauer, L.¹ Sladojevich, F.² Dixon, D.J.³

42
- 84869074395
- Z. K. Yu, W. W. Jin, Q. B. Jiang, Angew. Chem. 2012, 124, 6164-6177;
- (2012) Angew. Chem. , vol.124 , pp. 6164-6177
- Yu, Z.K.¹ Jin, W.W.² Jiang, Q.B.³

43
- 84862666912
- Angew. Chem. Int. Ed. 2012, 51, 6060-6072.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 6060-6072

44
- 84872744548
- Z. Du, Z. Shao, Chem. Soc. Rev. 2013, 42, 1337-1378.
- (2013) Chem. Soc. Rev. , vol.42 , pp. 1337-1378
- Du, Z.¹ Shao, Z.²

45
- 2942544978
- For the ionic hydrogenation mechanism, see: a) R. M. Bullock, Chem. Eur. J. 2004, 10, 2366-2374.
- (2004) Chem. Eur. J. , vol.10 , pp. 2366-2374
- Bullock, R.M.¹

46
- 19744370551
- H. R. Guan, M. Limura, M. P. Magee, J. R. Norton, G. Zhu, J. Am. Chem. Soc. 2005, 127, 7805-7814.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 7805-7814
- Guan, H.R.¹ Limura, M.² Magee, M.P.³ Norton, J.R.⁴ Zhu, G.⁵

47
- 81255195796
- M. Fleischmann, D. Drettwan, E. Sugiono, M. Reuping, R. M. Gschwind, Angew. Chem. 2011, 123, 6488-6493;
- (2011) Angew. Chem. , vol.123 , pp. 6488-6493
- Fleischmann, M.¹ Drettwan, D.² Sugiono, E.³ Reuping, M.⁴ Gschwind, R.M.⁵

48
- 79959896382
- Angew. Chem. Int. Ed. 2011, 50, 6364-6369.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 6364-6369

49
- 84885658568
- For mechanistic details, see: W. J. Tang, S. Johnston, J. Iggo, N. G. Berry, M. Phelan, L. Lian, J. Basca, J. L. Xiao, Angew. Chem. 2013, 125, 1712-1716;
- (2013) Angew. Chem. , vol.125 , pp. 1712-1716
- Tang, W.J.¹ Johnston, S.² Iggo, J.³ Berry, N.G.⁴ Phelan, M.⁵ Lian, L.⁶ Basca, J.⁷ Xiao, J.L.⁸

50
- 84873343015
- Angew. Chem. Int. Ed. 2013, 52, 1668-1672.
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 1668-1672

51
- 84885592100
- C. Q. Li, Ph.D. Thesis, University of Liverpool (UK), 2009
- C. Q. Li, Ph.D. Thesis, University of Liverpool (UK), 2009.

52
- 77749282354
- M. Klussmann, Angew. Chem. 2009, 121, 7260-7261;
- (2009) Angew. Chem. , vol.121 , pp. 7260-7261
- Klussmann, M.¹

53
- 70349894976
- Angew. Chem. Int. Ed. 2009, 48, 7124-7125.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7124-7125

54
- 33746182597
- For the organocatalytic reductive amination of ketones, see: a) S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590-7593;
- (2005) Angew. Chem. , vol.117 , pp. 7590-7593
- Hoffmann, S.¹ Seayad, A.M.² List, B.³

55
- 28044438742
- Angew. Chem. Int. Ed. 2005, 44, 7424-7427.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 7424-7427

56
- 30744477746
- R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84-86.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 84-86
- Storer, R.I.¹ Carrera, D.E.² Ni, Y.³ MacMillan, D.W.C.⁴

57
- 78149265083
- V. N. Wakchaure, M. Nicoletti, L. Ratjen, B. J. List, Synlett 2010, 2708-2710.
- (2010) Synlett , pp. 2708-2710
- Wakchaure, V.N.¹ Nicoletti, M.² Ratjen, L.³ List, B.J.⁴

58
- 78650828028
- V. N. Wakchaure, J. Zhou, S. Hoffmann, B. J. List, Angew. Chem. 2010, 122, 4716-4718;
- (2010) Angew. Chem. , vol.122 , pp. 4716-4718
- Wakchaure, V.N.¹ Zhou, J.² Hoffmann, S.³ List, B.J.⁴

59
- 77953948379
- Angew. Chem. Int. Ed. 2010, 49, 4612-4614.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 4612-4614

60
- 84859968484
- K. Saito, T. Akiyama, Chem. Commun. 2012, 48, 4573-4575.
- (2012) Chem. Commun. , vol.48 , pp. 4573-4575
- Saito, K.¹ Akiyama, T.²

61
- 78649844949
- M. Rueping, R. M. Koenigs, Chem. Commun. 2011, 47, 304-306.
- (2011) Chem. Commun. , vol.47 , pp. 304-306
- Rueping, M.¹ Koenigs, R.M.²

62
- 0000829650
- K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297-300;
- (1997) Angew. Chem. , vol.109 , pp. 297-300
- Haack, K.-J.¹ Hashiguchi, S.² Fujii, A.³ Ikariya, T.⁴ Noyori, R.⁵

63
- 0030984352
- Angew. Chem. Int. Ed. Engl. 1997, 36, 285-299.
- (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 285-299

64
- 33749516319
- Z. M. Heiden, B. J. Gorecki, T. B. Rauchfuss, J. Am. Chem. Soc. 2006, 128, 13048-13049.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 13048-13049
- Heiden, Z.M.¹ Gorecki, B.J.² Rauchfuss, T.B.³

65
- 33745933460
- T. Ohkuma, N. Utsumi, K. Tsutsumi, K. Murata, C. Sandoval, R. Noyori, J. Am. Chem. Soc. 2006, 128, 8724-8725.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 8724-8725
- Ohkuma, T.¹ Utsumi, N.² Tsutsumi, K.³ Murata, K.⁴ Sandoval, C.⁵ Noyori, R.⁶

66
- 36849018148
- T. Ohkuma, N. Utsumi, M. Watanabe, K. Tsutsumi, N. Arai, K. Murata, Org. Lett. 2007, 9, 2565-2567.
- (2007) Org. Lett. , vol.9 , pp. 2565-2567
- Ohkuma, T.¹ Utsumi, N.² Watanabe, M.³ Tsutsumi, K.⁴ Arai, N.⁵ Murata, K.⁶

67
- 68249143823
- Z. M. Heiden, B. J. Gorecki, T. B. Rauchfuss, J. Am. Chem. Soc. 2009, 131, 3593-3600.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 3593-3600
- Heiden, Z.M.¹ Gorecki, B.J.² Rauchfuss, T.B.³

68
- 28844477888
- For examples of catalysts containing substituted ethylene diamine li-gands, see: a) D. S. Matharu, D. J. Morris, A. M. Kawamoto, G. J. Clarkson, M. Wills, Org. Lett. 2005, 7, 5489-5491.
- (2005) Org. Lett. , vol.7 , pp. 5489-5491
- Matharu, D.S.¹ Morris, D.J.² Kawamoto, A.M.³ Clarkson, G.J.⁴ Wills, M.⁵

69
- 33746448277
- D. S. Matharu, D. J. Morris, G. J. Clarkson, M. Wills, Chem. Commun. 2006, 3232-3234.
- (2006) Chem. Commun. , pp. 3232-3234
- Matharu, D.S.¹ Morris, D.J.² Clarkson, G.J.³ Wills, M.⁴

70
- 54849442488
- D. S. Matharu, J. E. D. Martins, M. Wills, Chem. Asian J. 2008, 3, 1374-1383.
- (2008) Chem. Asian J. , vol.3 , pp. 1374-1383
- Matharu, D.S.¹ Martins, J.E.D.² Wills, M.³

71
- 64349112343
- J. E. D. Martins, G. J. Clarkson, M. Wills, Org. Lett. 2009, 11, 847-850.
- (2009) Org. Lett. , vol.11 , pp. 847-850
- Martins, J.E.D.¹ Clarkson, G.J.² Wills, M.³

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