SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 48, Issue 13, 2009, Pages 2367-2371

Highly efficient and regioselective platinum(ii)-Catalyzed tandem synthesisof multiply substituted indolines and tetrahydro-Quinolines

(2) Liu, Xin Yuan a Che, Chi Ming a

a UNIVERSITY OF HONG KONG (Hong Kong)

Author keywords

1,3 diketones; Aminoalkynes; Cyclization; Platinum; Synthetic methods

Indexed keywords

CATALYSIS; MOLECULAR SIEVES; PLATINUM;

1 ,3-DIKETONES; AMINOALKYNES; CHEMO-SELECTIVITY; MILD REACTION CONDITIONS; REGIO-SELECTIVE; SYNTHETIC METHODS; TANDEM CYCLIZATION; TETRAHYDROQUINOLINES;

CYCLIZATION;

INDOLE DERIVATIVE; INDOLINE; PLATINUM; QUINOLINE DERIVATIVE;

CATALYSIS; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CATALYSIS; CYCLIZATION; INDOLES; PLATINUM; QUINOLINES;

EID: 70349784860 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/anie.200805383 Document Type: Article

Times cited : (51)

References (61)

1
- 7044235263
- For recent reviews, see: a
- For recent reviews, see: a) L. F. Tietze, Chetn. Rev. 1996,96, 115-136;
- (1996) Chetn. Rev , vol.96 , pp. 115-136
- Tietze, L.F.¹

2
- 3242702454
- b) J. M. Lee, Y. Na, H. Han, S. Chang, Chem. Soc. Rev.2004, 33, 302-312;
- (2004) Chem. Soc. Rev , vol.33 , pp. 302-312
- Lee, J.M.¹ Na, Y.² Han, H.³ Chang, S.⁴

3
- 10944248645
- c) A. Ajamian, J. L. Gleason, Angew. Chem. 2004,116, 3842-3848;
- (2004) Angew. Chem , vol.116 , pp. 3842-3848
- Ajamian, A.¹ Gleason, J.L.²

4
- 4544376543
- Angew. Chem. Int. Ed. 2004, 43, 3754-3760;
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 3754-3760

5
- 17444401687
- d) J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem.Rev. 2005, 105, 1001-1020;
- (2005) Chem.Rev , vol.105 , pp. 1001-1020
- Wasilke, J.-C.¹ Obrey, S.J.² Baker, R.T.³ Bazan, G.C.⁴

6
- 20444486970
- e) A. deMeijere, P. von Zezschwitz, S. Bräse, Acc. Chem. Res.2005, 38, 413-422.
- (2005) Acc. Chem. Res , vol.38 , pp. 413-422
- deMeijere, A.¹ von Zezschwitz, P.² Bräse, S.³

7
- 84904236914
- For recent reviews on Au/Pt catalysis, see: a A. S. K. Hashmi, G. J.Hutchings, Angew. Chem. 2006, 118, 8064-8105;
- For recent reviews on Au/Pt catalysis, see: a) A. S. K. Hashmi, G. J.Hutchings, Angew. Chem. 2006, 118, 8064-8105;

8
- 33845546747
- Angew. Chem. Int. Ed. 2006, 45, 7896-7936;
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 7896-7936

9
- 34548635326
- b) A. Fiirstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519;
- (2007) Angew. Chem , vol.119 , pp. 3478-3519
- Fiirstner, A.¹ Davies, P.W.²

10
- 34250824768
- Angew. Chem. Int. Ed. 2007, 46, 3410-3449;
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 3410-3449

11
- 33947578482
- c) D. J. Gorin, F. D. Toste, Nature 2007, 446,395-403;
- (2007) Nature , vol.446 , pp. 395-403
- Gorin, D.J.¹ Toste, F.D.²

12
- 33846207883
- d) E. Jiménez-Núñez, A. M. Echavarren, Chem.Commun. 2007, 333-346;
- (2007) Chem.Commun , pp. 333-346
- Jiménez-Núñez, E.¹ Echavarren, A.M.²

13
- 52149110720
- e) N. Bongers, N. Krause, Angew. Chem. 2008, 120,2208-2211;
- (2008) Angew. Chem , vol.120 , pp. 2208-2211
- Bongers, N.¹ Krause, N.²

14
- 53249151254
- Angew. Chem. Int. Ed. 2008, 47, 2178-2181,
- (2008) Angew. Chem. Int. Ed , vol.47 , pp. 2178-2181

15
- 34547431140
- a) X.-Y. Liu, P. Ding, J.-S. Huang, C.-M. Che, Org. Lett.2007, 9, 2645-2648;
- (2007) Org. Lett , vol.9 , pp. 2645-2648
- Liu, X.-Y.¹ Ding, P.² Huang, J.-S.³ Che, C.-M.⁴

16
- 58549119469
- b) X.-Y. Liu, C.-M. Che, Angew. Chem. 2008, 120,3865-3870;
- (2008) Angew. Chem , vol.120 , pp. 3865-3870
- Liu, X.-Y.¹ Che, C.-M.²

17
- 45549104745
- Angew. Chem. Int. Ed. 2008, 47, 3805-3810.
- (2008) Angew. Chem. Int. Ed , vol.47 , pp. 3805-3810

18
- 1842637760
- a) J. J. Kennedy-Smith, S. T. Staben, F. D. Toste, J. Am. Chem.Soc. 2004, 126, 4526-4527;
- (2004) J. Am. Chem.Soc , vol.126 , pp. 4526-4527
- Kennedy-Smith, J.J.¹ Staben, S.T.² Toste, F.D.³

19
- 14244265392
- b) S. T. Staben, J. J. Kennedy-Smith, F. D. Toste, Angew. Chem.2004, 116, 5464-5466;
- (2004) Angew. Chem , vol.116 , pp. 5464-5466
- Staben, S.T.¹ Kennedy-Smith, J.J.² Toste, F.D.³

20
- 7244248645
- Angew. Chem. Int. Ed. 2004, 43, 5350-5352;
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 5350-5352

21
- 34547510627
- c) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211;
- (2007) Chem. Rev , vol.107 , pp. 3180-3211
- Hashmi, A.S.K.¹

22
- 51049121927
- d) Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108,3239-3265;
- (2008) Chem. Rev , vol.108 , pp. 3239-3265
- Li, Z.¹ Brouwer, C.² He, C.³

23
- 51049105959
- e) D. J. Gorin, B. D. Sherry, F. D. Toste, Chetn. Rev.2008, 108, 3351-3378;
- (2008) Chetn. Rev , vol.108 , pp. 3351-3378
- Gorin, D.J.¹ Sherry, B.D.² Toste, F.D.³

24
- 42749087843
- f) R. Skouta, C.-J. Li, Tetrahedron 2008, 64,4917-4938.
- (2008) Tetrahedron , vol.64 , pp. 4917-4938
- Skouta, R.¹ Li, C.-J.²

25
- 0000078290
- a) A. Arcadi, S. Di Giuseppe, F. Marinelli, E. Rossi, Adv. Synth.Catal. 2001, 343, 443-446;
- (2001) Adv. Synth.Catal , vol.343 , pp. 443-446
- Arcadi, A.¹ Di Giuseppe, S.² Marinelli, F.³ Rossi, E.⁴

26
- 0043154088
- b) A. Arcadi, G. Bianchi, S. Di Giuseppe, F. Marinelli, GreenChem. 2003, 5, 64-67.
- (2003) GreenChem , vol.5 , pp. 64-67
- Arcadi, A.¹ Bianchi, G.² Di Giuseppe, S.³ Marinelli, F.⁴

27
- 14244261063
- a) D. M. Volochnyuk, A. N. Kostyuk, D. A. Sibgatulin, A. N. Chernega,Tetrahedron, 2005, 61, 2839-2847;
- (2005) Tetrahedron , vol.61 , pp. 2839-2847
- Volochnyuk, D.M.¹ Kostyuk, A.N.² Sibgatulin, D.A.³ Chernega, A.N.⁴

28
- 33947142444
- b) D. A. Sibgatulin, D. M. Volochnyuk, A. N. Kostyuk, TetrahedronLett. 2007, 48, 2775-2779;
- (2007) TetrahedronLett , vol.48 , pp. 2775-2779
- Sibgatulin, D.A.¹ Volochnyuk, D.M.² Kostyuk, A.N.³

29
- 38849144528
- c) A. N. Kostyuk, D. M. Volochnyuk, D. A. Sibga-tulin, Synthesis2008, 161-184.
- (2008) Synthesis , pp. 161-184
- Kostyuk, A.N.¹ Volochnyuk, D.M.² Sibga-tulin, D.A.³

30
- 0001699963
- For selected examples, see: a
- For selected examples, see: a) D. L. Boger, C. W. Boyce, R. M. Garbaccio,J. A. Goldberg, Chem. Rev 1997, 97, 787-828;
- (1997) Chem. Rev , vol.97 , pp. 787-828
- Boger, D.L.¹ Boyce, C.W.² Garbaccio, R.M.³ Goldberg, J.A.⁴

31
- 0034620786
- b) T. Sunazuka, T. Hirose, T. Shirahata, Y. Harigaya, M. Hayashi, K.Komiyama, S. Ōmura, A. B. Smith III, J. Am. Chem. Soc. 2000,122, 2122-2123;
- (2000) J. Am. Chem. Soc , vol.122 , pp. 2122-2123
- Sunazuka, T.¹ Hirose, T.² Shirahata, T.³ Harigaya, Y.⁴ Hayashi, M.⁵ Komiyama, K.⁶ Ōmura, S.⁷ Smith III, A.B.⁸

32
- 22944450392
- c) A. B. Dounay, L. E. Overman, A. D. Wro-bleski, J. Am. Chem.Soc. 2005, 127, 10186-10187.
- (2005) J. Am. Chem.Soc , vol.127 , pp. 10186-10187
- Dounay, A.B.¹ Overman, L.E.² Wro-bleski, A.D.³

33
- 0020617280
- For selected examples, see: a
- For selected examples, see: a) N. Gruenfeld, J. L. Stanton, A. M. Yuan,F. H. Ebetino, L. J. Browne, C. Gude, C. F. Huebner, J. Med. Chem,.1983, 26, 1277-1282;
- (1983) J. Med. Chem , vol.26 , pp. 1277-1282
- Gruenfeld, N.¹ Stanton, J.L.² Yuan, A.M.³ Ebetino, F.H.⁴ Browne, L.J.⁵ Gude, C.⁶ Huebner, C.F.⁷

34
- 0030669049
- b) S. M. Bromidge, M. Duckworth, I. T. Forbes, P. Ham, F. D. King, K. M.Thewlis, F. E. Blaney, C. B. Naylor, T. P. Blackburn, G. A. Kennett, M. D. Wood,S. E. Clarke, J. Med. Chem. 1997, 40, 3494-3496;
- (1997) J. Med. Chem , vol.40 , pp. 3494-3496
- Bromidge, S.M.¹ Duckworth, M.² Forbes, I.T.³ Ham, P.⁴ King, F.D.⁵ Thewlis, K.M.⁶ Blaney, F.E.⁷ Naylor, C.B.⁸ Blackburn, T.P.⁹ Kennett, G.A.¹⁰ Wood, M.D.¹¹ Clarke, S.E.¹²

35
- 37049033626
- c) L. A. Hobson, W. A. Nugent, S. R. Anderson, S. S. Deshmukh, J. J.Haley III, P. Liu, N. A. Magnus, P. Sheeran, J. P. Sherbine, B. R. P. Stone, J.Zhu, Org. Process Res. Dev. 2007, 11, 985-995.
- (2007) Org. Process Res. Dev , vol.11 , pp. 985-995
- Hobson, L.A.¹ Nugent, W.A.² Anderson, S.R.³ Deshmukh, S.S.⁴ Haley III, J.J.⁵ Liu, P.⁶ Magnus, N.A.⁷ Sheeran, P.⁸ Sherbine, J.P.⁹ Stone, B.R.P.¹⁰ Zhu, J.¹¹

36
- 0032495775
- For examples of indoline syntheses, see: a K. Aoki, A. J. Peat, S. L.Buchwald, J. Am. Chem. Soc. 1998, 120, 3068-3073;
- For examples of indoline syntheses, see: a) K. Aoki, A. J. Peat, S. L.Buchwald, J. Am. Chem. Soc. 1998, 120, 3068-3073;

37
- 0034728665
- b) K. C. Nicolaou, A. J. Roecker, J. A. Pfefferkorn, G.-Q. Cao, J. Am.Chem. Soc. 2000, 122, 2966-2967;
- (2000) J. Am.Chem. Soc , vol.122 , pp. 2966-2967
- Nicolaou, K.C.¹ Roecker, A.J.² Pfefferkorn, J.A.³ Cao, G.-Q.⁴

38
- 0034686759
- c) G. S. Gil, U. M. Groth, J. Am. Chem. Soc. 2000, 122, 6789-6790;
- (2000) J. Am. Chem. Soc , vol.122 , pp. 6789-6790
- Gil, G.S.¹ Groth, U.M.²

39
- 7444269099
- d) R. Lira, J. P. Wolfe, J. Am. Chem. Soc. 2004,126, 13906-13907;
- (2004) J. Am. Chem. Soc , vol.126 , pp. 13906-13907
- Lira, R.¹ Wolfe, J.P.²

40
- 37249017443
- e) P. Thansandote, M. Raemy, A. Rudolph, M. Lautens, Org. Lett.2007, 9, 5255-5258;
- (2007) Org. Lett , vol.9 , pp. 5255-5258
- Thansandote, P.¹ Raemy, M.² Rudolph, A.³ Lautens, M.⁴

41
- 48849113342
- f) T. Watanabe, S. Oishi, N. Fujii, H. Ohno, Org. Lett.2008, 10, 1759-1762;
- (2008) Org. Lett , vol.10 , pp. 1759-1762
- Watanabe, T.¹ Oishi, S.² Fujii, N.³ Ohno, H.⁴

42
- 38949175721
- g) C. D. Gilmore, K. M. Allan, B. M. Stoltz, J. Am. Chem. Soc.2008, 130, 1558-1559;
- (2008) J. Am. Chem. Soc , vol.130 , pp. 1558-1559
- Gilmore, C.D.¹ Allan, K.M.² Stoltz, B.M.³

43
- 51649124289
- and references therein
- h) A. Minatti, S. L. Buchwald, Org. Lett. 2008, 10,2721-2724, and references therein.
- (2008) Org. Lett , vol.10 , pp. 2721-2724
- Minatti, A.¹ Buchwald, S.L.²

44
- 0000215352
- For examples, see: a
- For examples, see: a) D. L. Boger, R. S. Coleman, J. Org. Chem.1984, 49, 2240-2245;
- (1984) J. Org. Chem , vol.49 , pp. 2240-2245
- Boger, D.L.¹ Coleman, R.S.²

45
- 0000077067
- b) K. Hayakawa, T. Yasukouchi, K. Kanematsu, Tetrahedron Lett.1986, 27, 1837-1840;
- (1986) Tetrahedron Lett , vol.27 , pp. 1837-1840
- Hayakawa, K.¹ Yasukouchi, T.² Kanematsu, K.³

46
- 0037267658
- c) B. Witulski, J. Lumtscher, U. Bergsträßer, Synlett2003, 708-710;
- (2003) Synlett , pp. 708-710
- Witulski, B.¹ Lumtscher, J.² Bergsträßer, U.³

47
- 17744371152
- d) J. R. Dunetz, R. L. Danheiser, J. Am. Chem. Soc. 2005,127, 5776-5777.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 5776-5777
- Dunetz, J.R.¹ Danheiser, R.L.²

48
- 0030602266
- a) A. R. Katritzky, S. Rachwal, B. Rachwal, Tetrahedron1996, 52, 15031-15070;
- (1996) Tetrahedron , vol.52 , pp. 15031-15070
- Katritzky, A.R.¹ Rachwal, S.² Rachwal, B.³

49
- 0031721239
- b) V. Kouznetsov, A. Palma, C. Ewert, A. Varlamov, J. Heterocycl.Chem. 1998, 35, 761-785.
- (1998) J. Heterocycl.Chem , vol.35 , pp. 761-785
- Kouznetsov, V.¹ Palma, A.² Ewert, C.³ Varlamov, A.⁴

50
- 84904219636
- Structure determinations were performed by using NOESY experiments, seethe Supporting Information for details
- Structure determinations were performed by using NOESY experiments, seethe Supporting Information for details.

51
- 0000788623
- and references therein; For nucleophilic addition of amines on a C≡C bond which is mediatedby a platinum complexe, see: a
- For nucleophilic addition of amines on a C≡C bond which is mediatedby a platinum complexe, see: a) T.E. Müller, M. Beller, Chem. Rev.1998, 98, 675-704, and references therein;
- (1998) Chem. Rev , vol.98 , pp. 675-704
- Müller, T.E.¹ Beller, M.²

52
- 33751267070
- b) T. E. Müller, A.-K. Pleier, J. Chem. Soc. Dalton Trans.1999, 583-588;
- (1999) J. Chem. Soc. Dalton Trans , pp. 583-588
- Müller, T.E.¹ Pleier, A.-K.²

53
- 3042716544
- c) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. D. Milton, M. Hidai, S.Uemura, Angew. Chem. 2003, 115, 2785-2788;
- (2003) Angew. Chem , vol.115 , pp. 2785-2788
- Nishibayashi, Y.¹ Yoshikawa, M.² Inada, Y.³ Milton, M.D.⁴ Hidai, M.⁵ Uemura, S.⁶

54
- 0038112039
- Angew. Chem. Int. Ed. 2003, 42, 2681-2684.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 2681-2684

55
- 0037419450
- The 1,3-diketones can exist mostly as enols, see: A) E. Iglesias
- The 1,3-diketones can exist mostly as enols, see: a) E. Iglesias, J.Org. Chem. 2003, 68, 2680-2688;
- (2003) J.Org. Chem , vol.68 , pp. 2680-2688

56
- 33645456213
- b) S. Diezi, D. Ferri, A. Vargas, T. Mallat, A. Baiker, J. Am. Chem.Soc. 2006, 128, 4048-4057.
- (2006) J. Am. Chem.Soc , vol.128 , pp. 4048-4057
- Diezi, S.¹ Ferri, D.² Vargas, A.³ Mallat, T.⁴ Baiker, A.⁵

57
- 0034740925
- K. Funabiki, A. Isomura, Y. Yamaguchi, W. Hashimoto, K. Matsunaga, K.Shibata, M. Matsui, J. Chem. Soc. Perkin Trans. 1 2001, 2578-2582.
- (2001) J. Chem. Soc. Perkin Trans. 1 , pp. 2578-2582
- Funabiki, K.¹ Isomura, A.² Yamaguchi, Y.³ Hashimoto, W.⁴ Matsunaga, K.⁵ Shibata, K.⁶ Matsui, M.⁷

58
- 0000430183
- For platinum-catalyzed hydration of alkynes, see: a
- For platinum-catalyzed hydration of alkynes, see: a) W. Hiscox, P. W.Jennings, Organometallics 1990, 9, 1997-1999;
- (1990) Organometallics , vol.9 , pp. 1997-1999
- Hiscox, W.¹ Jennings, P.W.²

59
- 0000589215
- b) W. Baidossi, M. Lahav, J. Blum, J. Org. Chem. 1997,62, 669-672;
- (1997) J. Org. Chem , vol.62 , pp. 669-672
- Baidossi, W.¹ Lahav, M.² Blum, J.³

60
- 0038785249
- c) E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem.2002, 114, 4745-4747;
- (2002) Angew. Chem , vol.114 , pp. 4745-4747
- Mizushima, E.¹ Sato, K.² Hayashi, T.³ Tanaka, M.⁴

61
- 0041345498
- Angew. Chem. Int. Ed. 2002, 41, 4563-4565.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 4563-4565

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.