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Volumn , Issue 5, 2011, Pages 892-897

Chiral phosphoric acid catalyzed asymmetric Friedel-Crafts alkylation of indole with 3-hydroxyisoindolin-1-one: Enantioselective synthesis of 3-indolyl-substituted isoindolin-1-ones

(7) Yu, Xiaolei a Lu, Aidang a Wang, Youming a Wu, Guiping a Song, Haibin a Zhou, Zhenghong a Tang, Chuchi a

a NANKAI UNIVERSITY (China)

Author keywords

Alkylation; Enantioselectivity; Nitrogen heterocycles; Organocatalysis

Indexed keywords

EID: 79551558446 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.201001408 Document Type: Article

Times cited : (65)

References (48)

1
- 0032537535
- T. R. Belliotti, W. A. Brink, S. R. Kesten, Bioorg. Med. Chem. Lett. 1998, 8, 1499-1502.
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1499-1502
- Belliotti, T.R.¹ Brink, W.A.² Kesten, S.R.³

2
- 0026079335
- T. Wada, N. Fukuda, Psychopharmacology 1991, 103, 314-322.
- (1991) Psychopharmacology , vol.103 , pp. 314-322
- Wada, T.¹ Fukuda, N.²

3
- 0035969615
- J. R. Fuchs, R. L. Funk, Org. Lett. 2001, 3, 3923-3925.
- (2001) Org. Lett. , vol.3 , pp. 3923-3925
- Fuchs, J.R.¹ Funk, R.L.²

4
- 0025348717
- W. D. J. A. Norbert.
- R. Grigg, M. J. R. Dorrity, J. F. Malone, T. Mongkolaus-savaratana, W. D. J. A. Norbert, V. Sridharan, Tetrahedron Lett. 1990, 31, 3075-3076.
- (1990) Tetrahedron Lett. , vol.31 , pp. 3075-3076
- Grigg, R.¹ Dorrity, M.J.R.² Malone, J.F.³ Mongkolaus-Savaratana, T.⁴ Sridharan, V.⁵

5
- 0035680653
- D. Enders, V. Braig, G. Raabe, Can. J. Chem. 2001, 79, 1528.
- (2001) Can. J. Chem. , vol.79 , pp. 1528
- Enders, D.¹ Braig, V.² Raabe, G.³

6
- 15044348918
- L. Shen, R. P. Hsung, Org. Lett. 2005, 7, 775-778.
- (2005) Org. Lett. , vol.7 , pp. 775-778
- Shen, L.¹ Hsung, R.P.²

7
- 0037424819
- J. Clayden, C. J. Menet, Tetrahedron Lett. 2003, 44, 3059-3062.
- (2003) Tetrahedron Lett. , vol.44 , pp. 3059-3062
- Clayden, J.¹ Menet, C.J.²

8
- 0030908612
- S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, Tetrahedron Lett. 1997, 38, 3627-3630.
- (1997) Tetrahedron Lett. , vol.38 , pp. 3627-3630
- Allin, S.M.¹ Northfield, C.J.² Page, M.I.³ Slawin, A.M.Z.⁴

9
- 0032474793
- S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, Tetrahedron Lett. 1998, 39, 4905-4908.
- (1998) Tetrahedron Lett. , vol.39 , pp. 4905-4908
- Allin, S.M.¹ Northfield, C.J.² Page, M.I.³ Slawin, A.M.Z.⁴

10
- 0032889914
- S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, Tetrahedron Lett. 1999, 40, 141-142.
- (1999) Tetrahedron Lett. , vol.40 , pp. 141-142
- Allin, S.M.¹ Northfield, C.J.² Page, M.I.³ Slawin, A.M.Z.⁴

11
- 0032890444
- S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, Tetrahedron Lett. 1999, 40, 143-146.
- (1999) Tetrahedron Lett. , vol.40 , pp. 143-146
- Allin, S.M.¹ Northfield, C.J.² Page, M.I.³ Slawin, A.M.Z.⁴

12
- 0034616722
- S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, J. Chem. Soc. Perkin Trans. 1 2000, 1715-1721.
- (2000) J. Chem. Soc. Perkin Trans. 1 , pp. 1715-1721
- Allin, S.M.¹ Northfield, C.J.² Page, M.I.³ Slawin, A.M.Z.⁴

13
- 0041402770
- E. Deniau, D. Enders, A. Couture, P. Grandclaudon, Tetrahedron: Asymmetry 2003, 14, 2253-2258.
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2253-2258
- Deniau, E.¹ Enders, D.² Couture, A.³ Grandclaudon, P.⁴

14
- 0348230513
- A. A. Bahajaj, J. M. Vernon, G. D. Wilson, Tetrahedron 2004, 60, 1247-1253.
- (2004) Tetrahedron , vol.60 , pp. 1247-1253
- Bahajaj, A.A.¹ Vernon, J.M.² Wilson, G.D.³

15
- 0742306819
- M.-D. Chen, X. Zhou, M.-Z. He, Y.-P. Ruan, P.-Q. Huang, Tetrahedron 2004, 60, 1651-1657.
- (2004) Tetrahedron , vol.60 , pp. 1651-1657
- Chen, M.-D.¹ Zhou, X.² He, M.-Z.³ Ruan, Y.-P.⁴ Huang, P.-Q.⁵

16
- 58349112732
- E. Deniau, A. Couture, P. Grandclaudon, Tetrahedron: Asymmetry 2008, 19, 2735-2740.
- (2008) Tetrahedron: Asymmetry , vol.19 , pp. 2735-2740
- Deniau, E.¹ Couture, A.² Grandclaudon, P.³

17
- 0037124518
- J. Pérard-Viret, T. Prangé, A. Tomas, J. Royer, Tetrahedron 2002, 58, 5103-5108.
- (2002) Tetrahedron , vol.58 , pp. 5103-5108
- Pérard-Viret, J.¹ Prangé, T.² Tomas, A.³ Royer, J.⁴

18
- 12344317278
- D. L. Comins, S. Schilling, Y. Zhang, Org. Lett. 2005, 7, 95-98.
- (2005) Org. Lett. , vol.7 , pp. 95-98
- Comins, D.L.¹ Schilling, S.² Zhang, Y.³

19
- 38349022144
- M. Lamblin, A. Couture, E. Deniau, P. Grandclaudon, Tetrahedron: Asymmetry 2008, 19, 111-123.
- (2008) Tetrahedron: Asymmetry , vol.19 , pp. 111-123
- Lamblin, M.¹ Couture, A.² Deniau, E.³ Grandclaudon, P.⁴

20
- 19944413632
- M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Synlett 2005, 1199-1222.
- (2005) Synlett , pp. 1199-1222
- Bandini, M.¹ Melloni, A.² Tommasi, S.³ Umani-Ronchi, A.⁴

21
- 69249092514
- S.-L. You, Q. Cai, M. Zeng, Chem. Soc. Rev. 2009, 38, 2190-2201.
- (2009) Chem. Soc. Rev. , vol.38 , pp. 2190-2201
- You, S.-L.¹ Cai, Q.² Zeng, M.³

22
- 77953276740
- M. Zeng, S.-L. You, Synlett 2010, 1289-1301.
- (2010) Synlett , pp. 1289-1301
- Zeng, M.¹ You, S.-L.²

23
- 77951845524
- V. Terrasson, R. M. de Figueiredo, J. M. Campagne, Eur. J. Org. Chem. 2010, 2635-2655.
- (2010) Eur. J. Org. Chem. , pp. 2635-2655
- Terrasson, V.¹ De Figueiredo, R.M.² Campagne, J.M.³

24
- 0031689165
- M. Toyota, N. Ihara, Nat. Prod. Rep. 1998, 15, 327-340.
- (1998) Nat. Prod. Rep. , vol.15 , pp. 327-340
- Toyota, M.¹ Ihara, N.²

25
- 22944454156
- S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2920.
- (2005) Chem. Rev. , vol.105 , pp. 2873-2920
- Cacchi, S.¹ Fabrizi, G.²

26
- 33746864043
- G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875-2911.
- (2006) Chem. Rev. , vol.106 , pp. 2875-2911
- Humphrey, G.R.¹ Kuethe, J.T.²

27
- 71949117774
- Angew. Chem. Int. Ed. 2009, 48, 9608 - 9644.
- M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9786; Angew. Chem. Int. Ed. 2009, 48, 9608-9644.
- (2009) Angew. Chem. , vol.121 , pp. 9786
- Bandini, M.¹ Eichholzer, A.²

28
- 2342570203
- Angew. Chem. Int. Ed. 2004, 43, 1566 - 1568.
- For pioneering work, see: T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592; Angew. Chem. Int. Ed. 2004, 43, 1566-1568.
- (2004) Angew. Chem. , vol.116 , pp. 1592
- Akiyama, T.¹ Itoh, J.² Yokota, K.³ Fuchibe, K.⁴

29
- 2342521907
- D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 5356-5357
- Uraguchi, D.¹ Terada, M.²

30
- 77953261329
- For reviews on phosphoric acid catalysts, see: M. Terada, Synthesis 2010, 1929-1982.
- (2010) Synthesis , pp. 1929-1982
- Terada, M.¹

31
- 52049088477
- M. Terada, Chem. Commun. 2008, 4097-4112.
- (2008) Chem. Commun. , pp. 4097-4112
- Terada, M.¹

32
- 38349189109
- T. Akiyama, Chem. Rev. 2007, 107, 5744-5758.
- (2007) Chem. Rev. , vol.107 , pp. 5744-5758
- Akiyama, T.¹

33
- 33746272976
- Angew. Chem. Int. Ed. 2006, 45, 3909 - 3912.
- S. J. Connon, Angew. Chem. 2006, 118, 4013; Angew. Chem. Int. Ed. 2006, 45, 3909-3912.
- (2006) Angew. Chem. , vol.118 , pp. 4013
- Connon, S.J.¹

34
- 33745683617
- T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999-1010.
- (2006) Adv. Synth. Catal. , vol.348 , pp. 999-1010
- Akiyama, T.¹ Itoh, J.² Fuchibe, K.³

35
- 33745601363
- H. Y. Tang, G. F. Zhao, Z. H. Zhou, Q. L. Zhou, C. C. Tang, Tetrahedron Lett. 2006, 47, 5717-5721.
- (2006) Tetrahedron Lett. , vol.47 , pp. 5717-5721
- Tang, H.Y.¹ Zhao, G.F.² Zhou, Z.H.³ Zhou, Q.L.⁴ Tang, C.C.⁵

36
- 34548691690
- H. Y. Tang, P. Gao, G. F. Zhao, Z. H. Zhou, L. N. He, C. C. Tang, Catal. Commun. 2007, 8, 1811-1814.
- (2007) Catal. Commun. , vol.8 , pp. 1811-1814
- Tang, H.Y.¹ Gao, P.² Zhao, G.F.³ Zhou, Z.H.⁴ He, L.N.⁵ Tang, C.C.⁶

37
- 38049086667
- H. Y. Tang, G. F. Zhao, Z. H. Zhou, P. Gao, L. N. He, C. C. Tang, Eur. J. Org. Chem. 2008, 126-135.
- (2008) Eur. J. Org. Chem. , pp. 126-135
- Tang, H.Y.¹ Zhao, G.F.² Zhou, Z.H.³ Gao, P.⁴ He, L.N.⁵ Tang, C.C.⁶

38
- 48349136214
- H. Y. Tang, A. D. Lu, Z. H. Zhou, G. F. Zhao, L. N. He, C. C. Tang, Eur. J. Org. Chem. 2008, 1406-1410.
- (2008) Eur. J. Org. Chem. , pp. 1406-1410
- Tang, H.Y.¹ Lu, A.D.² Zhou, Z.H.³ Zhao, G.F.⁴ He, L.N.⁵ Tang, C.C.⁶

39
- 46949091946
- C. G. Wang, Z. H. Zhou, C. C. Tang, Org. Lett. 2008, 10, 1707-1710.
- (2008) Org. Lett. , vol.10 , pp. 1707-1710
- Wang, C.G.¹ Zhou, Z.H.² Tang, C.C.³

40
- 53849087875
- P. Gao, C. G. Wang, Y. Wu, Z. H. Zhou, C. C. Tang, Eur. J. Org. Chem. 2008, 4563-4566.
- (2008) Eur. J. Org. Chem. , pp. 4563-4566
- Gao, P.¹ Wang, C.G.² Wu, Y.³ Zhou, Z.H.⁴ Tang, C.C.⁵

41
- 50649124427
- A. D. Lu, X. Y. Xu, P. Gao, Z. H. Zhou, H. B. Song, C. C. Tang, Tetrahedron: Asymmetry 2008, 19, 1886-1890.
- (2008) Tetrahedron: Asymmetry , vol.19 , pp. 1886-1890
- Lu, A.D.¹ Xu, X.Y.² Gao, P.³ Zhou, Z.H.⁴ Song, H.B.⁵ Tang, C.C.⁶

42
- 68949152712
- A. D. Lu, P. Gao, Y. Wu, Y. M. Wang, Z. H. Zhou, C. C. Tang, Org. Biomol. Chem. 2009, 7, 3141-3147.
- (2009) Org. Biomol. Chem. , vol.7 , pp. 3141-3147
- Lu, A.D.¹ Gao, P.² Wu, Y.³ Wang, Y.M.⁴ Zhou, Z.H.⁵ Tang, C.C.⁶

43
- 72049119845
- K. Hu, C. G. Wang, X. P. Ma, Y. M. Wang, Z. H. Zhou, C. C. Tang, Tetrahedron: Asymmetry 2009, 20, 2178-2184.
- (2009) Tetrahedron: Asymmetry , vol.20 , pp. 2178-2184
- Hu, K.¹ Wang, C.G.² Ma, X.P.³ Wang, Y.M.⁴ Zhou, Z.H.⁵ Tang, C.C.⁶

44
- 77950231057
- A. D. Lu, R. H. Wu, Y. M. Wang, Z. H. Zhou, G. P. Wu, J. X. Fang, C. C. Tang, Eur. J. Org. Chem. 2010, 2057-2061.
- (2010) Eur. J. Org. Chem. , pp. 2057-2061
- Lu, A.D.¹ Wu, R.H.² Wang, Y.M.³ Zhou, Z.H.⁴ Wu, G.P.⁵ Fang, J.X.⁶ Tang, C.C.⁷

45
- 78249241240
- A. D. Lu, T. Liu, R. H. Wu, Y. M. Wang, Z. H. Zhou, G. P. Wu, J. X. Fang, C. C. Tang, Eur. J. Org. Chem. 2010, 5777-5781.
- (2010) Eur. J. Org. Chem. , pp. 5777-5781
- Lu, A.D.¹ Liu, T.² Wu, R.H.³ Wang, Y.M.⁴ Zhou, Z.H.⁵ Wu, G.P.⁶ Fang, J.X.⁷ Tang, C.C.⁸

46
- 78650838197
- A. D. Lu, R. H. Wu, Y. M. Wang, Z. H. Zhou, G. P. Wu, J. X. Fang, C. C. Tang, Eur. J. Org. Chem. 2011, 122-127.
- (2011) Eur. J. Org. Chem. , pp. 122-127
- Lu, A.D.¹ Wu, R.H.² Wang, Y.M.³ Zhou, Z.H.⁴ Wu, G.P.⁵ Fang, J.X.⁶ Tang, C.C.⁷

47
- 77949904394
- For a similar enantioselective Brànsted acid catalyzed nucleophilic substitution of Î-hydroxylactams with indole providing disubstituted Î-lactams, see.
- For a similar enantioselective Brànsted acid catalyzed nucleophilic substitution of Î-hydroxylactams with indole providing disubstituted Î-lactams, see:, M. Rueping, B. J. Nachtsheimb, Synlett 2010, 119-122.
- (2010) Synlett , pp. 119-122
- Rueping, M.¹ Nachtsheimb, B.J.²

48
- 79551572602
- CCDC-800015 (for 8a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
- CCDC-800015 (for 8a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.

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