SCOPUS 정보 검색 플랫폼

Chemical Communications

Volumn 49, Issue 85, 2013, Pages 10022-10024

Trichloromethyl ketones: Asymmetric transfer hydrogenation and subsequent Jocic-type reactions with amines

(6) Perryman, Michael S a Harris, Matthew E a Foster, Jade L a Joshi, Anushka a Clarkson, Guy J a Fox, David J a

a UNIVERSITY OF WARWICK (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINES; CATALYSIS; CHLOROFORM; HYDROGENATION; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RUTHENIUM; STEREOISOMERISM;

AMINE; KETONE DERIVATIVE; RUTHENIUM; TRICHLOROMETHYLKETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGENATION; JOCIC TYPE REACTION;

EID: 84885161650 PISSN: 13597345 EISSN: 1364548X Source Type: Journal
DOI: 10.1039/c3cc46070c Document Type: Article

Times cited : (39)

References (62)

1
- 0003416748
- Pergamon Press, Oxford
- R. M. Williams, Synthesis of Optically Acitve α-Amino Acids, Pergamon Press, Oxford, 1989
- (1989) Synthesis of Optically Acitve α-Amino Acids
- Williams, R.M.¹

2
- 58549085379
- D. V. Smil, S. Manku, Y. A. Chantigny, S. Leit, A. Wahhab, T. P. Yan, M. Fournel, C. Maroun, Z. Li, A.-M. Lemieux, A. Nicolescu, J. Rahil, S. Lefebvre, A. Panetta, J. M. Besterman, R. Déziel: Bioorg. Med. Chem. Lett. 2009 19: 688-692.
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 688-692
- Smil, D.V.¹ Manku, S.² Chantigny, Y.A.³ Leit, S.⁴ Wahhab, A.⁵ Yan, T.P.⁶ Fournel, M.⁷ Maroun, C.⁸ Li, Z.⁹ Lemieux, A.-M.¹⁰ Nicolescu, A.¹¹ Rahil, J.¹² Lefebvre, S.¹³ Panetta, A.¹⁴ Besterman, J.M.¹⁵ Déziel, R.¹⁶

3
- 0038546886
- D.-S. Su, M. K. Markowitz, R. M. DiPardo, K. L. Murphy, C. M. Harrell, S. S. O'Malley, R. W. Ransom, R. S. L. Chang, S. Ha, F. J. Hess, D. J. Pettibone, G. S. Mason, S. Boyce, R. M. Freidinger, M. G. Bock: J. Am. Chem. Soc. 2003 125: 7516-7517.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 7516-7517
- Su, D.-S.¹ Markowitz, M.K.² Dipardo, R.M.³ Murphy, K.L.⁴ Harrell, C.M.⁵ O'malley, S.S.⁶ Ransom, R.W.⁷ Chang, R.S.L.⁸ Ha, S.⁹ Hess, F.J.¹⁰ Pettibone, D.J.¹¹ Mason, G.S.¹² Boyce, S.¹³ Freidinger, R.M.¹⁴ Bock, M.G.¹⁵

4
- 34248998744
- J. Ren, C. E. Nichols, P. P. Chamberlain, K. L. Weaver, S. A. Short, J. H. Chan, J.-P. Kleim, D. K. Stammers: J. Med. Chem. 2007 50: 2301-2309.
- (2007) J. Med. Chem , vol.50 , pp. 2301-2309
- Ren, J.¹ Nichols, C.E.² Chamberlain, P.P.³ Weaver, K.L.⁴ Short, S.A.⁵ Chan, J.H.⁶ Kleim, J.-P.⁷ Stammers, D.K.⁸

5
- 33847632984
- G.-B. Liang, X. Qian, D. Feng, T. Biftu, G. Eiermann, H. He, B. Leiting, K. Lyons, A. Petrov, R. Sinha-Roy, B. Zhang, J. Wu, X. Zhang, N. A. Thornberry, A. E. Weber: Bioorg. Med. Chem. Lett. 2007 17: 1903-1907.
- (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 1903-1907
- Liang, G.-B.¹ Qian, X.² Feng, D.³ Biftu, T.⁴ Eiermann, G.⁵ He, H.⁶ Leiting, B.⁷ Lyons, K.⁸ Petrov, A.⁹ Sinha-Roy, R.¹⁰ Zhang, B.¹¹ Wu, J.¹² Zhang, X.¹³ Thornberry, N.A.¹⁴ Weber, A.E.¹⁵

6
- 84865028402
- S.-Y. B. Hsieh, M. Kreituss, I. Bode, W. Jeffrey: Chem. Commun. 2012 48: 8892-8894.
- (2012) Chem. Commun , vol.48 , pp. 8892-8894
- Hsieh, S.-Y.B.¹ Kreituss, M.² Bode, I.³ Jeffrey, W.⁴

7
- 79960576703
- J. I. Jang, S. Y. Kang, K. H. Kang, Y. S. Park: Tetrahedron 2011 67: 6221-6226.
- (2011) Tetrahedron , vol.67 , pp. 6221-6226
- Jang, J.I.¹ Kang, S.Y.² Kang, K.H.³ Park, Y.S.⁴

8
- 84885149491
- R. Holl, D. Schepmann, B. Wünsch: MedChemComm 2012 3: 673-679.
- (2012) Medchemcomm , vol.3 , pp. 673-679
- Holl, R.¹ Schepmann, D.² Wünsch, B.³

9
- 0037325675
- J. Seibel, D. Brown, A. Amour, S. J. Macdonald, N. J. Oldham, C. J. Schofield: Bioorg. Med. Chem. Lett. 2003 13: 387-389.
- (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 387-389
- Seibel, J.¹ Brown, D.² Amour, A.³ Macdonald, S.J.⁴ Oldham, N.J.⁵ Schofield, C.J.⁶

10
- 17844390143
- G. P. Pollini, N. Baricordi, S. Benetti, C. De Risi, V. Zanirato: Tetrahedron Lett. 2005 46: 3699-3701.
- (2005) Tetrahedron Lett , vol.46 , pp. 3699-3701
- Pollini, G.P.¹ Baricordi, N.² Benetti, S.³ De Risi, C.⁴ Zanirato, V.⁵

11
- 78349253782
- S. Tanimori, H. Kashiwagi, T. Nishimura, M. Kirihata: Adv. Synth. Catal. 2010 352: 2531-2537.
- (2010) Adv. Synth. Catal , vol.352 , pp. 2531-2537
- Tanimori, S.¹ Kashiwagi, H.² Nishimura, T.³ Kirihata, M.⁴

12
- 0344451807
- Z. Jocic: Zh. Russ. Fiz.-Khim. O-va. 1897 29: 97.
- (1897) Zh. Russ. Fiz.-Khim. O-Va , vol.29 , pp. 97
- Jocic, Z.¹

13
- 1542635908
- G. Bargellini: Gazz. Chim. Ital. 1906 36: 329.
- (1906) Gazz. Chim. Ital , vol.36 , pp. 329
- Bargellini, G.¹

14
- 33947435775
- S. M. McElvain, C. L. Stevens: J. Am. Chem. Soc. 1947 69: 2667-2670.
- (1947) J. Am. Chem. Soc , vol.69 , pp. 2667-2670
- McElvain, S.M.¹ Stevens, C.L.²

15
- 0001015116
- C. Weizmann, M. Sulzbacher, E. Bergmann: J. Am. Chem. Soc. 1948 70: 1153-1158.
- (1948) J. Am. Chem. Soc , vol.70 , pp. 1153-1158
- Weizmann, C.¹ Sulzbacher, M.² Bergmann, E.³

16
- 0001897610
- W. Reeve, J. R. McKee, R. Brown, S. Lakshmanan, G. A. McKee: Can. J. Chem. 1980 58: 485-493.
- (1980) Can. J. Chem , vol.58 , pp. 485-493
- Reeve, W.¹ McKee, J.R.² Brown, R.³ Lakshmanan, S.⁴ McKee, G.A.⁵

17
- 84868089915
- T. S. Snowden: ARKIVOC 2012: 24-40.
- (2012) ARKIVOC , pp. 24-40
- Snowden, T.S.¹

18
- 2342459736
- W. Reeve, C. W. Woods: J. Am. Chem. Soc. 1960 82: 4062-4066.
- (1960) J. Am. Chem. Soc , vol.82 , pp. 4062-4066
- Reeve, W.¹ Woods, C.W.²

19
- 0009604226
- W. Reeve, E. L. Compere: J. Am. Chem. Soc. 1961 83: 2755-2759.
- (1961) J. Am. Chem. Soc , vol.83 , pp. 2755-2759
- Reeve, W.¹ Compere, E.L.²

20
- 33846307782
- J. L. Shamshina, T. S. Snowden: Org. Lett. 2006 8: 5881-5884.
- (2006) Org. Lett , vol.8 , pp. 5881-5884
- Shamshina, J.L.¹ Snowden, T.S.²

21
- 2342536449
- W. Reeve, M. Nees: J. Am. Chem. Soc. 1967 89: 647-651.
- (1967) J. Am. Chem. Soc , vol.89 , pp. 647-651
- Reeve, W.¹ Nees, M.²

22
- 2342489880
- J. Blanchet, J. Zhu: Tetrahedron Lett. 2004 45: 4449-4452.
- (2004) Tetrahedron Lett , vol.45 , pp. 4449-4452
- Blanchet, J.¹ Zhu, J.²

23
- 0008587197
- J. T. Lai: J. Org. Chem. 1980 45: 3671-3673.
- (1980) J. Org. Chem , vol.45 , pp. 3671-3673
- Lai, J.T.¹

24
- 61349100108
- L. R. Cafiero, T. S. Snowden: Org. Lett. 2008 10: 3853-3856.
- (2008) Org. Lett , vol.10 , pp. 3853-3856
- Cafiero, L.R.¹ Snowden, T.S.²

25
- 84981756533
- G. Korger: Chem. Ber. 1963 96: 10-37.
- (1963) Chem. Ber , vol.96 , pp. 10-37
- Korger, G.¹

26
- 49849101904
- J. T. Lai: Synthesis 1982: 71-74.
- (1982) Synthesis , pp. 71-74
- Lai, J.T.¹

27
- 26844443331
- R. J. Cvetovich, J. Y. L. Chung, M. H. Kress, J. S. Amato, L. Matty, M. D. Weingarten, F.-R. Tsay, Z. Li, G. Zhou: J. Org. Chem. 2005 70: 8560-8563.
- (2005) J. Org. Chem , vol.70 , pp. 8560-8563
- Cvetovich, R.J.¹ Chung, J.Y.L.² Kress, M.H.³ Amato, J.S.⁴ Matty, L.⁵ Weingarten, M.D.⁶ Tsay, F.-R.⁷ Li, Z.⁸ Zhou, G.⁹

28
- 63749099000
- K. J. Butcher, J. Hurst: Tetrahedron Lett. 2009 50: 2497-2500.
- (2009) Tetrahedron Lett , vol.50 , pp. 2497-2500
- Butcher, K.J.¹ Hurst, J.²

29
- 64349084679
- G. Liu, D. Romo: Org. Lett. 2009 11: 1143-1146.
- (2009) Org. Lett , vol.11 , pp. 1143-1146
- Liu, G.¹ Romo, D.²

30
- 37049105516
- H. Wynberg, E. G. J. Staring: J. Chem. Soc., Chem. Commun. 1984: 1181-1182.
- (1984) J. Chem. Soc., Chem. Commun , pp. 1181-1182
- Wynberg, H.¹ Staring, E.G.J.²

31
- 77049106925
- P. S. Tiseni, R. Peters: Chem.-Eur. J. 2010 16: 2503-2517.
- (2010) Chem.-Eur. J , vol.16 , pp. 2503-2517
- Tiseni, P.S.¹ Peters, R.²

32
- 84989540865
- E. J. Corey, J. O. Link: J. Am. Chem. Soc. 1992 114: 1906-1908.
- (1992) J. Am. Chem. Soc , vol.114 , pp. 1906-1908
- Corey, E.J.¹ Link, J.O.²

33
- 0035808942
- C. Mellin-Morli”re, D. J. Aitken, S. D. Bull, S. G. Davies, H.-P. Husson: Tetrahedron: Asymmetry 2001 12: 149-155.
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 149-155
- Mellin-Morli”re, C.¹ Aitken, D.J.² Bull, S.D.³ Davies, S.G.⁴ Husson, H.-P.⁵

34
- 0030048684
- A. P. Khrimian, J. E. Oliver, R. M. Waters, S. Panicker, J. M. Nicholson, J. A. Klun: Tetrahedron: Asymmetry 1996 7: 37-40.
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 37-40
- Khrimian, A.P.¹ Oliver, J.E.² Waters, R.M.³ Panicker, S.⁴ Nicholson, J.M.⁵ Klun, J.A.⁶

35
- 0026751962
- E. J. Corey, J. O. Link: Tetrahedron Lett. 1992 33: 3431-3434.
- (1992) Tetrahedron Lett , vol.33 , pp. 3431-3434
- Corey, E.J.¹ Link, J.O.²

36
- 0001119728
- H. Wynberg, E. G. J. Staring: J. Am. Chem. Soc. 1982 104: 166-168.
- (1982) J. Am. Chem. Soc , vol.104 , pp. 166-168
- Wynberg, H.¹ Staring, E.G.J.²

37
- 0028101178
- C. E. Song, T. H. Ryu, E. J. Rob, I. O. Kim, H.-J. Ha: Tetrahedron: Asymmetry 1994 5: 1215-1218.
- (1994) Tetrahedron: Asymmetry , vol.5 , pp. 1215-1218
- Song, C.E.¹ Ryu, T.H.² Rob, E.J.³ Kim, I.O.⁴ Ha, H.-J.⁵

38
- 3042839768
- B. Jiang, Y.-G. Si: Adv. Synth. Catal. 2004 346: 669-674.
- (2004) Adv. Synth. Catal , vol.346 , pp. 669-674
- Jiang, B.¹ Si, Y.-G.²

39
- 0001226063
- K. Maruoka, Y. Hoshino, T. Shirasaka, H. Yamamoto: Tetrahedron Lett. 1988 29: 3967-3970.
- (1988) Tetrahedron Lett , vol.29 , pp. 3967-3970
- Maruoka, K.¹ Hoshino, Y.² Shirasaka, T.³ Yamamoto, H.⁴

40
- 82255192393
- B. Lygo, C. Davison, T. Evans, J. A. R. Gilks, J. Leonard, C.-E. Roy: Tetrahedron 2011 67: 10164-10170.
- (2011) Tetrahedron , vol.67 , pp. 10164-10170
- Lygo, B.¹ Davison, C.² Evans, T.³ Gilks, J.A.R.⁴ Leonard, J.⁵ Roy, C.-E.⁶

41
- 10244274184
- T. Ooi, T. Miura, K. Ohmatsu, A. Saito, K. Maruoka: Org. Biomol. Chem. 2004 2: 3312-3319.
- (2004) Org. Biomol. Chem , vol.2 , pp. 3312-3319
- Ooi, T.¹ Miura, T.² Ohmatsu, K.³ Saito, A.⁴ Maruoka, K.⁵

42
- 34250787504
- P. V. Ramachandran, B. Gong, A. V. Teodorović: J. Fluorine Chem. 2007 128: 844-850.
- (2007) J. Fluorine Chem , vol.128 , pp. 844-850
- Ramachandran, P.V.¹ Gong, B.² Teodorović, A.V.³

43
- 33644660116
- J. S. M. Samec, J.-E. Backvall, P. G. Andersson, P. Brandt: Chem. Soc. Rev. 2006 35: 237-248.
- (2006) Chem. Soc. Rev , vol.35 , pp. 237-248
- Samec, J.S.M.¹ Backvall, J.-E.² Andersson, P.G.³ Brandt, P.⁴

44
- 0029879373
- A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori: J. Am. Chem. Soc. 1996 118: 2521-2522.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 2521-2522
- Fujii, A.¹ Hashiguchi, S.² Uematsu, N.³ Ikariya, T.⁴ Noyori, R.⁵

45
- 0001040853
- S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori: J. Am. Chem. Soc. 1995 117: 7562-7563.
- (1995) J. Am. Chem. Soc , vol.117 , pp. 7562-7563
- Hashiguchi, S.¹ Fujii, A.² Takehara, J.³ Ikariya, T.⁴ Noyori, R.⁵

46
- 0002123299
- R. Noyori, S. Hashiguchi: Acc. Chem. Res. 1997 30: 97-102.
- (1997) Acc. Chem. Res , vol.30 , pp. 97-102
- Noyori, R.¹ Hashiguchi, S.²

47
- 19744373802
- A. M. Hayes, D. J. Morris, G. J. Clarkson, M. Wills: J. Am. Chem. Soc. 2005 127: 7318-7319.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 7318-7319
- Hayes, A.M.¹ Morris, D.J.² Clarkson, G.J.³ Wills, M.⁴

48
- 35948969131
- F. K. Cheung, C. Lin, F. Minissi, A. L. Crivillé, M. A. Graham, D. J. Fox, M. Wills: Org. Lett. 2007 9: 4659-4662.
- (2007) Org. Lett , vol.9 , pp. 4659-4662
- Cheung, F.K.¹ Lin, C.² Minissi, F.³ Crivillé, A.L.⁴ Graham, M.A.⁵ Fox, D.J.⁶ Wills, M.⁷

49
- 76749119482
- F. K. Cheung, A. J. Clarke, G. J. Clarkson, D. J. Fox, M. A. Graham, C. Lin, A. L. Criville, M. Wills: Dalton Trans. 2010 39: 1395-1402.
- (2010) Dalton Trans , vol.39 , pp. 1395-1402
- Cheung, F.K.¹ Clarke, A.J.² Clarkson, G.J.³ Fox, D.J.⁴ Graham, M.A.⁵ Lin, C.⁶ Criville, A.L.⁷ Wills, M.⁸

50
- 0030984352
- K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori: Angew. Chem., Int. Ed. Engl. 1997 36: 285-288.
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 285-288
- Haack, K.-J.¹ Hashiguchi, S.² Fujii, A.³ Ikariya, T.⁴ Noyori, R.⁵

51
- 0033999757
- M. Yamakawa, H. Ito, R. Noyori: J. Am. Chem. Soc. 2000 122: 1466-1478.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 1466-1478
- Yamakawa, M.¹ Ito, H.² Noyori, R.³

52
- 0035800369
- M. Yamakawa, I. Yamada, R. Noyori: Angew. Chem., Int. Ed. 2001 40: 2818-2821.
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2818-2821
- Yamakawa, M.¹ Yamada, I.² Noyori, R.³

53
- 33947362823
- J.-W. Handgraaf, E. J. Meijer: J. Am. Chem. Soc. 2007 129: 3099-3103.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 3099-3103
- Handgraaf, J.-W.¹ Meijer, E.J.²

54
- 84872123436
- A. A. Granovsky, Firefly version 7.1.G, www.http://classic.chem.msu.su/gran/firefly/index.html
- Firefly
- Granovsky, A.A.¹

55
- 79952943559
- S. Grimme, S. Ehrlich, L. Goerigk: J. Comput. Chem. 2011 32: 1456-1465.
- (2011) J. Comput. Chem , vol.32 , pp. 1456-1465
- Grimme, S.¹ Ehrlich, S.² Goerigk, L.³

56
- 26244461462
- F. Weigend, R. Ahlrichs: Phys. Chem. Chem. Phys. 2005: 3297-3305.
- (2005) Phys. Chem. Chem. Phys , pp. 3297-3305
- Weigend, F.¹ Ahlrichs, R.²

57
- 0345732575
- D. Šterk, M. S. Stephan, B. Mohar: Tetrahedron Lett. 2004 45: 535-537.
- (2004) Tetrahedron Lett , vol.45 , pp. 535-537
- Šterk, D.¹ Stephan, M.S.² Mohar, B.³

58
- 33846143169
- D. Šterk, M. Stephan, B. Mohar: Org. Lett. 2006 8: 5935-5938.
- (2006) Org. Lett , vol.8 , pp. 5935-5938
- Šterk, D.¹ Stephan, M.² Mohar, B.³

59
- 79959735902
- S. V. Slungård, T.-A. Krakeli, T. H. K. Thvedt, E. Fuglseth, E. Sundby, B. H. Hoff: Tetrahedron 2011 67: 5642-5650.
- (2011) Tetrahedron , vol.67 , pp. 5642-5650
- Slungård, S.V.¹ Krakeli, T.-A.² Thvedt, T.H.K.³ Fuglseth, E.⁴ Sundby, E.⁵ Hoff, B.H.⁶

60
- 0037122705
- D. J. Fox, J. Reckless, S. G. Warren, D. J. Grainger: J. Med. Chem. 2002 45: 360-370.
- (2002) J. Med. Chem , vol.45 , pp. 360-370
- Fox, D.J.¹ Reckless, J.² Warren, S.G.³ Grainger, D.J.⁴

61
- 13444292881
- D. J. Fox, J. Reckless, S. M. Wilbert, I. Greig, S. Warren, D. J. Grainger: J. Med. Chem. 2005 48: 867-874.
- (2005) J. Med. Chem , vol.48 , pp. 867-874
- Fox, D.J.¹ Reckless, J.² Wilbert, S.M.³ Greig, I.⁴ Warren, S.⁵ Grainger, D.J.⁶

62
- 66749154773
- D. J. Fox, J. Reckless, H. Lingard, S. Warren, D. J. Grainger: J. Med. Chem. 2009 52: 3591-3595.
- (2009) J. Med. Chem , vol.52 , pp. 3591-3595
- Fox, D.J.¹ Reckless, J.² Lingard, H.³ Warren, S.⁴ Grainger, D.J.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.