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Volumn 11, Issue 40, 2013, Pages 6984-6993

Acid-catalyzed reactions of 3-hydroxy-2-oxindoles with electron-rich substrates: Synthesis of 2-oxindoles with all-carbon quaternary center

(6) Kinthada, Lakshmana K a Ghosh, Santanu a De, Subhadip a Bhunia, Subhajit a Dey, Dhananjay a Bisai, Alakesh a

a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH BHOPAL (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONES; ACID-CATALYZED REACTIONS; ELECTRON-RICH; LEWIS ACID-CATALYZED REACTIONS; PHENYLACETYLENES; QUATERNARY CENTERS;

KETONES; STYRENE;

CARBON;

EID: 84884695530 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c3ob41482e Document Type: Article

Times cited : (44)

References (58)

1
- 84889375944
- ed., Wiley,; For numerous examples, see
- Quaternary Stereocenters. Challenges and Solutions in Organic Synthesis, ed., J. Christoffers, and, A. Baro, Wiley, 2006; For numerous examples, see
- (2006) Quaternary Stereocenters. Challenges and Solutions in Organic Synthesis
- Christoffers, J.¹ Baro, A.²

2
- 0042261072
- Wiley-VCH, Weinheim, 1st edn,; For a review, see
- K. C. Nicolaou and J. S. Chen, Classics in Total Synthesis III, Wiley-VCH, Weinheim, 1st edn, 2011; For a review, see
- (2011) Classics in Total Synthesis III
- Nicolaou, K.C.¹ Chen, J.S.²

3
- 0002979399
- K. C. Nicolaou D. Vourloumis N. Winssinger P. S. Baran Angew. Chem., Int. Ed. 2000 39 44
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 44
- Nicolaou, K.C.¹ Vourloumis, D.² Winssinger, N.³ Baran, P.S.⁴

4
- 0037414970
- H. Lin S. J. Danishefsky Angew. Chem., Int. Ed. 2003 42 36
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 36
- Lin, H.¹ Danishefsky, S.J.²

5
- 1842732181
- J. F. Austin S.-G. Kim C. J. Sinz W.-J. Xiao D. W. C. MacMillan Proc. Natl. Acad. Sci. U. S. A. 2004 101 5482
- (2004) Proc. Natl. Acad. Sci. U. S. A. , vol.101 , pp. 5482
- Austin, J.F.¹ Kim, S.-G.² Sinz, C.J.³ Xiao, W.-J.⁴ Macmillan, D.W.C.⁵

6
- 52449100159
- J. T. Mohr M. R. Krout B. M. Stoltz Nature 2008 455 323
- (2008) Nature , vol.455 , pp. 323
- Mohr, J.T.¹ Krout, M.R.² Stoltz, B.M.³

7
- 79955900405
- For reviews, see
- B. M. Trost S. Malhotra W. H. Chan J. Am. Chem. Soc. 2011 133 7328
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 7328
- Trost, B.M.¹ Malhotra, S.² Chan, W.H.³

8
- 1842851813
- C. J. Douglas L. E. Overman Proc. Natl. Acad. Sci. U. S. A. 2004 101 5363
- (2004) Proc. Natl. Acad. Sci. U. S. A. , vol.101 , pp. 5363
- Douglas, C.J.¹ Overman, L.E.²

9
- 70449382104
- B. M. Trost M. K. Brennan Synthesis 2009 3003
- (2009) Synthesis , pp. 3003
- Trost, B.M.¹ Brennan, M.K.²

10
- 77954271846
- F. Zhou Y.-L. Liu J. Zhou Adv. Synth. Catal. 2010 352 1381
- (2010) Adv. Synth. Catal. , vol.352 , pp. 1381
- Zhou, F.¹ Liu, Y.-L.² Zhou, J.³

11
- 77955674388
- A. Millemaggi R. J. K. Taylor Eur. J. Org. Chem. 2010 4527
- (2010) Eur. J. Org. Chem. , pp. 4527
- Millemaggi, A.¹ Taylor, R.J.K.²

12
- 0043288716
- ed. A. Brossi, Academic Press, New York, 1-75
- T. Hino and M. Nakagawa, The Alkaloids: Chemistry and Pharmacology, ed., A. Brossi, Academic Press, New York, 1989, vol. 34, pp. 1-75
- (1989) The Alkaloids: Chemistry and Pharmacology , vol.34
- Hino, T.¹ Nakagawa, M.²

13
- 77957077902
- ed. S. W. Pelletier, Pergamon, London, 163-236; For reviews of pyrroloindoline natural products, see
- U. Anthoni, C. Christophersen and P. H. Nielsen, Alkaloids Chemical and Biological Perspectives, ed., S. W. Pelletier, Pergamon, London, 1999, vol. 13, pp. 163-236; For reviews of pyrroloindoline natural products, see
- (1999) Alkaloids Chemical and Biological Perspectives , vol.13
- Anthoni, U.¹ Christophersen, C.² Nielsen, P.H.³

14
- 34547166889
- A. Steven L. E. Overman Angew. Chem., Int. Ed. 2007 46 5488
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 5488
- Steven, A.¹ Overman, L.E.²

15
- 0001586671
- ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, ch. 1.8
- G. A. Olah, R. Krishnamurti and G. K. S. Prakash, in Comprehensive Organic Synthesis, ed., B. M. Trost, and, I. Fleming, Pergamon Press, Oxford, 1991, ch. 1.8, vol. 3, pp. 293-339
- (1991) Comprehensive Organic Synthesis , vol.3 , pp. 293-339
- Olah, G.A.¹ Krishnamurti, R.² Prakash, G.K.S.³

16
- 33846199064
- ed. R. A. Sheldon and H. Bekkum, Wiley-VCH, New York
- G. R. Meima, G. S. Lee and J. M. Garces, in Friedel-Crafts Alkylation, ed., R. A. Sheldon, and, H. Bekkum, Wiley-VCH, New York, 2001, pp. 151-160
- (2001) Friedel-Crafts Alkylation , pp. 151-160
- Meima, G.R.¹ Lee, G.S.² Garces, J.M.³

17
- 69249092514
- For photo-Fries and related rearrangement to access 3,3-unsymmetrically substituted 2-oxindoles, see
- S.-L. You Q. Cai M. Zeng Chem. Soc. Rev. 2009 38 2190
- (2009) Chem. Soc. Rev. , vol.38 , pp. 2190
- You, S.-L.¹ Cai, Q.² Zeng, M.³

18
- 26444521578
- F. W. Goldberg P. Magnus R. Turnbull Org. Lett. 2005 7 4531
- (2005) Org. Lett. , vol.7 , pp. 4531
- Goldberg, F.W.¹ Magnus, P.² Turnbull, R.³

19
- 35248823162
- C.-M. Cheung F. W. Goldberg P. Magnus C. J. Russell R. Turnbull V. Lynch J. Am. Chem. Soc. 2007 129 12320
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 12320
- Cheung, C.-M.¹ Goldberg, F.W.² Magnus, P.³ Russell, C.J.⁴ Turnbull, R.⁵ Lynch, V.⁶

20
- 33747237680
- P. Magnus R. Turnbull Org. Lett. 2006 8 3497
- (2006) Org. Lett. , vol.8 , pp. 3497
- Magnus, P.¹ Turnbull, R.²

21
- 85172393015
- A. Baeyer M. J. Lazarus Chem. Ber. 1885 18 2637
- (1885) Chem. Ber. , vol.18 , pp. 2637
- Baeyer, A.¹ Lazarus, M.J.²

22
- 7344228964
- For related approaches, see
- D. A. Klumpp K. Yeung G. K. S. Prakash G. A. Olah J. Org. Chem. 1998 63 4481
- (1998) J. Org. Chem. , vol.63 , pp. 4481
- Klumpp, D.A.¹ Yeung, K.² Prakash, G.K.S.³ Olah, G.A.⁴

23
- 1842450535
- A. Natarajan Y.-H. Fan H. Chen Y. Guo J. Iyasere F. Harbinski W. J. Christ H. Aktas J. A. Halperin J. Med. Chem. 2004 47 1882
- (2004) J. Med. Chem. , vol.47 , pp. 1882
- Natarajan, A.¹ Fan, Y.-H.² Chen, H.³ Guo, Y.⁴ Iyasere, J.⁵ Harbinski, F.⁶ Christ, W.J.⁷ Aktas, H.⁸ Halperin, J.A.⁹

24
- 77956399208
- M. C. G. Hernandez M. G. Zolotukhin S. Fomine G. Cedillo S. L. Morales Macromolecules 2010 43 6968
- (2010) Macromolecules , vol.43 , pp. 6968
- Hernandez, M.C.G.¹ Zolotukhin, M.G.² Fomine, S.³ Cedillo, G.⁴ Morales, S.L.⁵

25
- 77957891703
- M. K. Christensen K. D. Erichsen C. Trojel-Hansen J. Tjørnelund S. J. Nielsen K. Frydenvang T. N. Johansen B. Nielsen M. Sehested P. B. Jensen M. Ikaunieks A. Zaichenko E. Loza I. Kalvinsh F. Bjorkling J. Med. Chem. 2010 53 7140
- (2010) J. Med. Chem. , vol.53 , pp. 7140
- Christensen, M.K.¹ Erichsen, K.D.² Trojel-Hansen, C.³ Tjørnelund, J.⁴ Nielsen, S.J.⁵ Frydenvang, K.⁶ Johansen, T.N.⁷ Nielsen, B.⁸ Sehested, M.⁹ Jensen, P.B.¹⁰ Ikaunieks, M.¹¹ Zaichenko, A.¹² Loza, E.¹³ Kalvinsh, I.¹⁴ Bjorkling, F.¹⁵

26
- 33846031951
- J. S. Yadav B. V. SubbaReddy K. U. Gayathri S. Meraj A. R. Prasad Synthesis 2006 4121
- (2006) Synthesis , pp. 4121
- Yadav, J.S.¹ Subbareddy, B.V.² Gayathri, K.U.³ Meraj, S.⁴ Prasad, A.R.⁵

27
- 5644298630
- K. C. Nicolaou D. Y.-K. Chen X. Huang T. Ling M. Bella S. A. Snyder J. Am. Chem. Soc. 2004 126 12888
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 12888
- Nicolaou, K.C.¹ Chen, D.Y.-K.² Huang, X.³ Ling, T.⁴ Bella, M.⁵ Snyder, S.A.⁶

28
- 34848889987
- D. B. England G. Merey A. Padwa Org. Lett. 2007 9 3805
- (2007) Org. Lett. , vol.9 , pp. 3805
- England, D.B.¹ Merey, G.² Padwa, A.³

29
- 40749099452
- D. B. England G. Merey A. Padwa Heterocycles 2007 74 491
- (2007) Heterocycles , vol.74 , pp. 491
- England, D.B.¹ Merey, G.² Padwa, A.³

30
- 80054696871
- I. Gorokhovik L. Neuville J. Zhu Org. Lett. 2011 13 5536
- (2011) Org. Lett. , vol.13 , pp. 5536
- Gorokhovik, I.¹ Neuville, L.² Zhu, J.³

31
- 84255169381
- F. Zhou Z.-Y. Cao J. Zhang H.-B. Yang J. Zhou Chem.-Asian J. 2012 7 233
- (2012) Chem.-Asian J. , vol.7 , pp. 233
- Zhou, F.¹ Cao, Z.-Y.² Zhang, J.³ Yang, H.-B.⁴ Zhou, J.⁵

32
- 84867459848
- L. Chen J. Zhou Chem.-Asian J. 2012 7 2510
- (2012) Chem.-Asian J. , vol.7 , pp. 2510
- Chen, L.¹ Zhou, J.²

33
- 84860603664
- L. Chen F. Zhou T.-D. Shi J. Zhou J. Org. Chem. 2012 77 4354
- (2012) J. Org. Chem. , vol.77 , pp. 4354
- Chen, L.¹ Zhou, F.² Shi, T.-D.³ Zhou, J.⁴

34
- 84875836336
- 4-catalyzed Ritter reactions of 3-hydroxy-2-oxindoles, see
- C. Piemontesi Q. Wang J. Zhu Org. Biomol. Chem. 2013 11 1533
- (2013) Org. Biomol. Chem. , vol.11 , pp. 1533
- Piemontesi, C.¹ Wang, Q.² Zhu, J.³

35
- 84859223006
- For the synthesis of 3-substituted 3-(alkylthio)/alkoxyoxindoles, see
- F. Zhou M. Ding J. Zhou Org. Biomol. Chem. 2012 10 3178
- (2012) Org. Biomol. Chem. , vol.10 , pp. 3178
- Zhou, F.¹ Ding, M.² Zhou, J.³

36
- 84867336857
- F. Zhu F. Zhou Z.-Y. Cao C. Wang Y.-X. Zhang C.-H. Wang J. Zhou Synthesis 2012 3129
- (2012) Synthesis , pp. 3129
- Zhu, F.¹ Zhou, F.² Cao, Z.-Y.³ Wang, C.⁴ Zhang, Y.-X.⁵ Wang, C.-H.⁶ Zhou, J.⁷

37
- 84866432553
- 3-mediated reactions in total synthesis of indole alkaloids, see
- S. Ghosh L. K. Kinthada S. Bhunia A. Bisai Chem. Commun. 2012 10132
- (2012) Chem. Commun. , pp. 10132
- Ghosh, S.¹ Kinthada, L.K.² Bhunia, S.³ Bisai, A.⁴

38
- 1942489302
- J. R. Fuchs R. L. Funk J. Am. Chem. Soc. 2004 126 5068
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 5068
- Fuchs, J.R.¹ Funk, R.L.²

39
- 14844363196
- J. R. Fuchs R. L. Funk Org. Lett. 2005 7 677
- (2005) Org. Lett. , vol.7 , pp. 677
- Fuchs, J.R.¹ Funk, R.L.²

40
- 84867557708
- J. Belmer R. L. Funk J. Am. Chem. Soc. 2012 134 16941
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 16941
- Belmer, J.¹ Funk, R.L.²

41
- 33750591952
- C. Menozzi P. I. Dalko J. Cossy Chem. Commun. 2006 4638
- (2006) Chem. Commun. , pp. 4638
- Menozzi, C.¹ Dalko, P.I.² Cossy, J.³

42
- 34548825098
- For enantioselective approaches, see
- S. Krishnan B. M. Stoltz Tetrahedron Lett. 2007 48 7571
- (2007) Tetrahedron Lett. , vol.48 , pp. 7571
- Krishnan, S.¹ Stoltz, B.M.²

43
- 70350014973
- S. Ma X. Han S. Krishnan S. C. Virgil B. M. Stoltz Angew. Chem., Int. Ed. 2009 48 8037
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 8037
- Ma, S.¹ Han, X.² Krishnan, S.³ Virgil, S.C.⁴ Stoltz, B.M.⁵

44
- 84871566588
- J. Zuo Y.-H. Liao X.-M. Zhang W.-C. Yuan J. Org. Chem. 2012 77 11325
- (2012) J. Org. Chem. , vol.77 , pp. 11325
- Zuo, J.¹ Liao, Y.-H.² Zhang, X.-M.³ Yuan, W.-C.⁴

45
- 84870939700
- S. Ghosh S. De B. N. Kakde S. Bhunia A. Adhikary A. Bisai Org. Lett. 2012 14 5864
- (2012) Org. Lett. , vol.14 , pp. 5864
- Ghosh, S.¹ De, S.² Kakde, B.N.³ Bhunia, S.⁴ Adhikary, A.⁵ Bisai, A.⁶

46
- 84877902361
- For discussions on silyl-stabilized β-carbocations, see
- S. Bhunia S. Ghosh D. Dey A. Bisai Org. Lett. 2013 15 2426
- (2013) Org. Lett. , vol.15 , pp. 2426
- Bhunia, S.¹ Ghosh, S.² Dey, D.³ Bisai, A.⁴

47
- 0003787137
- Wiley, London, p. 81
- I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976, p. 81
- (1976) Frontier Orbitals and Organic Chemical Reactions
- Fleming, I.¹

48
- 10044225138
- J. B. Lambert Tetrahedron 1990 46 2627
- (1990) Tetrahedron , vol.46 , pp. 2627
- Lambert, J.B.¹

49
- 0032900270
- Acetonitrile is reported as a good solvent for F-C alkylations, Ritter reactions (as solvent and reagent), and substitution with heteroatoms at elevated temperature, see: ref. 6d and 7a,b
- J. B. Lambert Y. Zhao R. W. Emblidge L. A. Salvador X. Liu J.-H. So E. C. Chelius Acc. Chem. Res. 1999 32 183
- (1999) Acc. Chem. Res. , vol.32 , pp. 183
- Lambert, J.B.¹ Zhao, Y.² Emblidge, R.W.³ Salvador, L.A.⁴ Liu, X.⁵ So, J.-H.⁶ Chelius, E.C.⁷

50
- 69449089744
- N. Duguet A. M. Z. Slawin A. D. Smith Org. Lett. 2009 11 3858
- (2009) Org. Lett. , vol.11 , pp. 3858
- Duguet, N.¹ Slawin, A.M.Z.² Smith, A.D.³

51
- 84861838320
- E. Richmond N. Duguet A. M. Z. Slawin T. Lébl A. D. Smith Org. Lett. 2012 14 2762
- (2012) Org. Lett. , vol.14 , pp. 2762
- Richmond, E.¹ Duguet, N.² Slawin, A.M.Z.³ Lébl, T.⁴ Smith, A.D.⁵

52
- 79955369063
- J. E. DeLorbe S. Y. Jabri S. M. Mennen L. E. Overman F.-L. Zhang J. Am. Chem. Soc. 2011 133 6549
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 6549
- Delorbe, J.E.¹ Jabri, S.Y.² Mennen, S.M.³ Overman, L.E.⁴ Zhang, F.-L.⁵

53
- 84862907571
- 2 (condition C) in chloroform at 50 °C (12 h) afforded ± 16a in 58% and 60% yield, respectively For the isolation and synthesis of alkaloid trisindole (16e), see
- C. Guo J. Song J.-Z. Huang P.-H. Chen S.-W. Luo L.-Z. Gong Angew. Chem., Int. Ed. 2012 51 1046
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 1046
- Guo, C.¹ Song, J.² Huang, J.-Z.³ Chen, P.-H.⁴ Luo, S.-W.⁵ Gong, L.-Z.⁶

54
- 0028603513
- 3-catalyzed self-addition, see
- M. Kobayashi S. Aoki K. Gato K. Matsunami M. Kurosu I. Kitagawa Chem. Pharm. Bull. 1994 42 2449
- (1994) Chem. Pharm. Bull. , vol.42 , pp. 2449
- Kobayashi, M.¹ Aoki, S.² Gato, K.³ Matsunami, K.⁴ Kurosu, M.⁵ Kitagawa, I.⁶

55
- 26844433958
- For a related approach, see
- B. Pal V. S. Giri P. Jaisankar Catal. Commun. 2005 6 711
- (2005) Catal. Commun. , vol.6 , pp. 711
- Pal, B.¹ Giri, V.S.² Jaisankar, P.³

56
- 4544281153
- For the synthesis of 3-hydroxy-2-oxindole 8e, see
- K. Fujino E. Yanase Y. Shinoda S. Nakatsuka Biosci. Biotechnol. Biochem. 2004 68 764
- (2004) Biosci. Biotechnol. Biochem. , vol.68 , pp. 764
- Fujino, K.¹ Yanase, E.² Shinoda, Y.³ Nakatsuka, S.⁴

57
- 0030032246
- U. Berens J. M. Brown J. Long R. Selke Tetrahedron: Asymmetry 1996 7 285
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 285
- Berens, U.¹ Brown, J.M.² Long, J.³ Selke, R.⁴

58
- 77954317442
- P. Chauhan S. S. Chimni Chem.-Eur. J. 2010 16 7709
- (2010) Chem.-Eur. J. , vol.16 , pp. 7709
- Chauhan, P.¹ Chimni, S.S.²

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