SCOPUS 정보 검색 플랫폼

Volumn 18, Issue 21, 2012, Pages 6470-6474

Brønsted acid catalyzed cycloisomerizations of 5,2-enyne-1-ones: Highly regioselective synthesis of 2,3-dihydro-4H-pyran-4-ones

(7) Yang, Fang a Ji, Ke Gong a Zhao, Shu Chun a Ali, Shaukat a Ye, Yu Ying a Liu, Xue Yuan a Liang, Yong Min a

a LANZHOU UNIVERSITY (China)

Author keywords

Br nsted acid; cyclization; dihydropyranones; dual catalyst; enynes

Indexed keywords

ALKENE MOIETIES; CYCLOISOMERIZATIONS; DIHYDROPYRANONES; ENYNES; REGIO-SELECTIVE; REGIOSELECTIVE SYNTHESIS;

CATALYSTS; CYCLIZATION; OLEFINS; REGIOSELECTIVITY;

CATALYSIS;

ALKYNE; PYRONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKYNES; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PYRONES; STEREOISOMERISM;

EID: 84861135678 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201103771 Document Type: Article

Times cited : (22)

References (60)

1
- 2542523876
- V. Dumontet, N. V. Hung, M.-T. Adeline, C. Riche, A. Chiaroni, T. Se'venet, F. Gue'ritte, J. Nat. Prod. 2004, 67, 858-862
- (2004) J. Nat. Prod. , vol.67 , pp. 858-862
- Dumontet, V.¹ Hung, N.V.² Adeline, M.-T.³ Riche, C.⁴ Chiaroni, A.⁵ Se'Venet, T.⁶ Gue'Ritte, F.⁷

2
- 33645506481
- J.-Y. Zhang, Y. Li, W.-K. Wang, X.-G. She, X.-F. Pan, J. Org. Chem. 2006, 71, 2918-2921.
- (2006) J. Org. Chem. , vol.71 , pp. 2918-2921
- Zhang, J.-Y.¹ Li, Y.² Wang, W.-K.³ She, X.-G.⁴ Pan, X.-F.⁵

3
- 0027429137
- F. Kiuchi, Y. Goto, Y. Sugimoto, N. Akao, K. Kondo, Y. Tsuda, Chem. Pharm. Bull. 1993, 41, 1640-1643
- (1993) Chem. Pharm. Bull. , vol.41 , pp. 1640-1643
- Kiuchi, F.¹ Goto, Y.² Sugimoto, Y.³ Akao, N.⁴ Kondo, K.⁵ Tsuda, Y.⁶

4
- 65349194989
- K. Yamada, K. Subeki Nabeta, M. Yamasaki, K. Katakura, H. Matsuura, Biosci. Biotechnol. Biochem. 2009, 73, 776-780.
- (2009) Biosci. Biotechnol. Biochem. , vol.73 , pp. 776-780
- Yamada, K.¹ Nabeta, K.S.² Yamasaki, M.³ Katakura, K.⁴ Matsuura, H.⁵

5
- 0000570755
- S. Danishefsky, J. F. Kerwin, Jr., S. Kobayashi, J. Am. Chem. Soc. 1982, 104, 358-360
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 358-360
- Danishefsky, S.¹ Kerwin Jr., J.F.² Kobayashi, S.³

6
- 0001283316
- S. Danishefsky, N. Kato, D. Askin, J. F. Kerwin, Jr., J. Am. Chem. Soc. 1982, 104, 360.
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 360
- Danishefsky, S.¹ Kato, N.² Askin, D.³ Kerwin Jr., J.F.⁴

7
- 0003257831
- S. Danishefsky, E. R. Larson, D. Askin, J. Am. Chem. Soc. 1982, 104, 6457-6458
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 6457-6458
- Danishefsky, S.¹ Larson, E.R.² Askin, D.³

8
- 0001659060
- S. J. Danishefsky, M. T. Biolodeau, Angew. Chem. 1996, 108, 1482-1522
- (1996) Angew. Chem. , vol.108 , pp. 1482-1522
- Danishefsky, S.J.¹ Biolodeau, M.T.²

9
- 0029739240
- Angew. Chem. Int. Ed. Engl. 1996, 35, 1380-1419
- (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1380-1419

10
- 0000595175
- I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063-2192
- (1997) Chem. Rev. , vol.97 , pp. 2063-2192
- Fleming, I.¹ Barbero, A.² Walter, D.³

11
- 0033717307
- M. M. Faul, B. E. Huff, Chem. Rev. 2000, 100, 2407-2473
- (2000) Chem. Rev. , vol.100 , pp. 2407-2473
- Faul, M.M.¹ Huff, B.E.²

12
- 0037414319
- Y. Yamashita, S. Saito, H. Ishitani, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3793-3798
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 3793-3798
- Yamashita, Y.¹ Saito, S.² Ishitani, H.³ Kobayashi, S.⁴

13
- 0037442892
- D. R. Williams, R. W. Heidebrecht, J. Am. Chem. Soc. 2003, 125, 1843-1850.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 1843-1850
- Williams, D.R.¹ Heidebrecht, R.W.²

14
- 0012049418
- S. Danishefsky, D. F. Harvey, G. Quallich, B. J. Uang, J. Org. Chem. 1984, 49, 392-393
- (1984) J. Org. Chem. , vol.49 , pp. 392-393
- Danishefsky, S.¹ Harvey, D.F.² Quallich, G.³ Uang, B.J.⁴

15
- 84856549574
- K. A. Jørgensen, Angew. Chem. 2000, 112, 3702-3733
- (2000) Angew. Chem. , vol.112 , pp. 3702-3733
- Jørgensen, K.A.¹

16
- 0034675619
- Angew. Chem. Int. Ed. 2000, 39, 3558-3588
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3558-3588

17
- 0028886765
- G. E. Keck, X.-Y. Li, D. Krishnamurthy, J. Org. Chem. 1995, 60, 5998-5999
- (1995) J. Org. Chem. , vol.60 , pp. 5998-5999
- Keck, G.E.¹ Li, X.-Y.² Krishnamurthy, D.³

18
- 33750490438
- F. Silva, M. Reiter, R. Mills-Webb, M. Sawicki, D. Klär, N. Bensel, A. Wagner, V. Gouverneur, J. Org. Chem. 2006, 71, 8390-8394
- (2006) J. Org. Chem. , vol.71 , pp. 8390-8394
- Silva, F.¹ Reiter, M.² Mills-Webb, R.³ Sawicki, M.⁴ Klär, D.⁵ Bensel, N.⁶ Wagner, A.⁷ Gouverneur, V.⁸

19
- 31944439407
- B. Gao, Z. Yua, Z. Fua, X. Fenga, Tetrahedron Lett. 2006, 47, 1537-1539
- (2006) Tetrahedron Lett. , vol.47 , pp. 1537-1539
- Gao, B.¹ Yua, Z.² Fua, Z.³ Fenga, X.⁴

20
- 0037198746
- G. G. Zipp, M. A. Hilfiker, S. G. Nelson, Org. Lett. 2002, 4, 1823-1826
- (2002) Org. Lett. , vol.4 , pp. 1823-1826
- Zipp, G.G.¹ Hilfiker, M.A.² Nelson, S.G.³

21
- 20544445733
- J. D. Winkler, K. Oh, Org. Lett. 2005, 7, 2421-2423
- (2005) Org. Lett. , vol.7 , pp. 2421-2423
- Winkler, J.D.¹ Oh, K.²

22
- 80051705187
- D. A. Astashko, V. I. Tyvorskii, Tetrahedron Lett. 2011, 52, 4792-4794
- (2011) Tetrahedron Lett. , vol.52 , pp. 4792-4794
- Astashko, D.A.¹ Tyvorskii, V.I.²

23
- 0742269535
- M. Reiter, S. Ropp, V. Gouverneur, Org. Lett. 2004, 6, 91-94
- (2004) Org. Lett. , vol.6 , pp. 91-94
- Reiter, M.¹ Ropp, S.² Gouverneur, V.³

24
- 33749001732
- M. Reiter, H. Turner, V. Gouverneur, Chem. Eur. J. 2006, 12, 7190-7203
- (2006) Chem. Eur. J. , vol.12 , pp. 7190-7203
- Reiter, M.¹ Turner, H.² Gouverneur, V.³

25
- 68349129686
- M. Schuler, F. Silva, C. Bobbio, A. Tessier, V. Gouverneur, Angew. Chem. 2008, 120, 8045-8048
- (2008) Angew. Chem. , vol.120 , pp. 8045-8048
- Schuler, M.¹ Silva, F.² Bobbio, C.³ Tessier, A.⁴ Gouverneur, V.⁵

26
- 54749120024
- Angew. Chem. Int. Ed. 2008, 47, 7927-7930.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7927-7930

27
- 34249807049
- H. Wang, B. J. Shuhler, M. Xian, J. Org. Chem. 2007, 72, 4280-4283
- (2007) J. Org. Chem. , vol.72 , pp. 4280-4283
- Wang, H.¹ Shuhler, B.J.² Xian, M.³

28
- 70249104301
- F. K. MacDonald, D. J. Burnell, J. Org. Chem. 2009, 74, 6973-6979
- (2009) J. Org. Chem. , vol.74 , pp. 6973-6979
- MacDonald, F.K.¹ Burnell, D.J.²

29
- 65449176745
- R. Ahmad, R. A. Khera, A. Villinger, P. Langer, Tetrahedron Lett. 2009, 50, 3020-3022
- (2009) Tetrahedron Lett. , vol.50 , pp. 3020-3022
- Ahmad, R.¹ Khera, R.A.² Villinger, A.³ Langer, P.⁴

30
- 75149132026
- P. C. Andrews, W. J. Gee, P. C. Junk, H. Krautscheid, Org. Biomol. Chem. 2010, 8, 698-705
- (2010) Org. Biomol. Chem. , vol.8 , pp. 698-705
- Andrews, P.C.¹ Gee, W.J.² Junk, P.C.³ Krautscheid, H.⁴

31
- 77956896933
- R. A. Khera, R. Ahmad, I. Ullah, O. U. R. Abid, O. Fatunsin, M. Sher, A. Villinger, P. Langer, Helv. Chim. Acta 2010, 93, 1705-1715.
- (2010) Helv. Chim. Acta , vol.93 , pp. 1705-1715
- Khera, R.A.¹ Ahmad, R.² Ullah, I.³ Abid, O.U.R.⁴ Fatunsin, O.⁵ Sher, M.⁶ Villinger, A.⁷ Langer, P.⁸

32
- 2942557280
- I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198
- (2004) Chem. Rev. , vol.104 , pp. 2127-2198
- Nakamura, I.¹ Yamamoto, Y.²

33
- 54849171800
- V. Michelet, P. Y. Toullec, J. P. Gentêt, Angew. Chem. 2008, 120, 4338-4386
- (2008) Angew. Chem. , vol.120 , pp. 4338-4386
- Michelet, V.¹ Toullec, P.Y.² Gentêt, J.P.³

34
- 46649098072
- Angew. Chem. Int. Ed. 2008, 47, 4268-4315
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4268-4315

35
- 51049097913
- E. Jiménez-Núńez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350
- (2008) Chem. Rev. , vol.108 , pp. 3326-3350
- Jiménez-Núńez, E.¹ Echavarren, A.M.²

36
- 70350014173
- A. S. K. Hashmi, M. Rudolph, J. Huck, W. Frey, J. W. Bats, M. Hamzić, Angew. Chem. 2009, 121, 5962-5966
- (2009) Angew. Chem. , vol.121 , pp. 5962-5966
- Hashmi, A.S.K.¹ Rudolph, M.² Huck, J.³ Frey, W.⁴ Bats, J.W.⁵ Hamzić, M.⁶

37
- 70349898694
- Angew. Chem. Int. Ed. 2009, 48, 5848-5852
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5848-5852

38
- 80054969722
- X.-Z. Shu, S.-Y. Huang, D.-X. Shu, I. A. Guzei, W.-P. Tang, Angew. Chem. 2011, 123, 8303-8306
- (2011) Angew. Chem. , vol.123 , pp. 8303-8306
- Shu, X.-Z.¹ Huang, S.-Y.² Shu, D.-X.³ Guzei, I.A.⁴ Tang, W.-P.⁵

39
- 80051776993
- Angew. Chem. Int. Ed. 2011, 50, 8153-8156.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 8153-8156

40
- 52049110849
- X.-Z. Shu, X.-Y. Liu, K.-G. Ji, H.-Q. Xiao, Y.-M. Liang, Chem. Eur. J. 2008, 14, 5282-5289.
- (2008) Chem. Eur. J. , vol.14 , pp. 5282-5289
- Shu, X.-Z.¹ Liu, X.-Y.² Ji, K.-G.³ Xiao, H.-Q.⁴ Liang, Y.-M.⁵

41
- 79954598427
- Synthesis of the substrate: see the Supporting Information or the procedure reported in the literature
- Synthesis of the substrate: see the Supporting Information or the procedure reported in the literature:, F. Yang, K.-G. Ji, H.-T. Zhu, A. Shaukat, X.-Y. Liu, Y.-M. Liang, Chem. Eur. J. 2011, 17, 4986-4990.
- (2011) Chem. Eur. J. , vol.17 , pp. 4986-4990
- Yang, F.¹ Ji, K.-G.² Zhu, H.-T.³ Shaukat, A.⁴ Liu, X.-Y.⁵ Liang, Y.-M.⁶

42
- 37049105311
- R. O. C. Norman, W. J. E. Parr, C. B. Thomas, J. Chem. Soc. Perkin Trans. 1 1976, 1983-1987
- (1976) J. Chem. Soc. Perkin Trans. 1 , pp. 1983-1987
- Norman, R.O.C.¹ Parr, W.J.E.² Thomas, C.B.³

43
- 33751500525
- Y. Fukuda, K. Utimoto, J. Org. Chem. 1991, 56, 3729-3731
- (1991) J. Org. Chem. , vol.56 , pp. 3729-3731
- Fukuda, Y.¹ Utimoto, K.²

44
- 0001459366
- J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. 1998, 110, 1475-1478
- (1998) Angew. Chem. , vol.110 , pp. 1475-1478
- Teles, J.H.¹ Brode, S.² Chabanas, M.³

45
- 0032486218
- Angew. Chem. Int. Ed. 1998, 37, 1415-1418
- (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1415-1418

46
- 66149171362
- C. Sperger, A. Fiksdahl, Org. Lett. 2009, 11, 2449-2452.
- (2009) Org. Lett. , vol.11 , pp. 2449-2452
- Sperger, C.¹ Fiksdahl, A.²

47
- 38349189109
- T. Akiyama, Chem. Rev. 2007, 107, 5744-5758
- (2007) Chem. Rev. , vol.107 , pp. 5744-5758
- Akiyama, T.¹

48
- 53849094456
- Y.-h. Liu, S.-l. Zhou, G.-j. Li, B. Yan, S.-h. Guo, Y.-b. Zhou, H. Zhang, P. G. Wang, Adv. Synth. Catal. 2008, 350, 797-801
- (2008) Adv. Synth. Catal. , vol.350 , pp. 797-801
- Liu, Y.-H.¹ Zhou, S.-L.² Li, G.-J.³ Yan, B.⁴ Guo, S.-H.⁵ Zhou, Y.-B.⁶ Zhang, H.⁷ Wang, P.G.⁸

49
- 74549214428
- T. Jin, M. Himuro, Y. Yamamoto, Angew. Chem. 2009, 121, 6007-6010
- (2009) Angew. Chem. , vol.121 , pp. 6007-6010
- Jin, T.¹ Himuro, M.² Yamamoto, Y.³

50
- 67650578694
- T. Jin, F. Yang, C. Liu, Y. Yamamoto, Chem. Commun. 2009, 3533-3535
- (2009) Chem. Commun. , pp. 3533-3535
- Jin, T.¹ Yang, F.² Liu, C.³ Yamamoto, Y.⁴

51
- 69249116093
- Y. Yamamoto, I. D. Gridnev, N. T. Patil, T. Jin, Chem. Commun. 2009, 5075-5087
- (2009) Chem. Commun. , pp. 5075-5087
- Yamamoto, Y.¹ Gridnev, I.D.² Patil, N.T.³ Jin, T.⁴

52
- 77952564588
- T. Jin, M. Himuro, Y. Yamamoto, J. Am. Chem. Soc. 2010, 132, 5590-5591.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 5590-5591
- Jin, T.¹ Himuro, M.² Yamamoto, Y.³

53
- 0002627233
- H. J. Reich, S. Wollowitz, Org. React. 1993, 44, 1-296
- (1993) Org. React. , vol.44 , pp. 1-296
- Reich, H.J.¹ Wollowitz, S.²

54
- 33847768650
- N. Daryabari, T. Akbarzadeh, M. Amini, R. Miri, H. Mirkhani, A. Shafiee, J. Iran. Chem. Soc. 2007, 4, 30-36
- (2007) J. Iran. Chem. Soc. , vol.4 , pp. 30-36
- Daryabari, N.¹ Akbarzadeh, T.² Amini, M.³ Miri, R.⁴ Mirkhani, H.⁵ Shafiee, A.⁶

55
- 13444302555
- J. D. Winkler, E. C. McLaughlin, Org. Lett. 2005, 7, 227-229.
- (2005) Org. Lett. , vol.7 , pp. 227-229
- Winkler, J.D.¹ McLaughlin, E.C.²

56
- 77955898850
- A. Mendoza, P. Pardo, F. Rodríguez, F, Fañanás, Chem. Eur. J. 2010, 16, 9758-9762
- (2010) Chem. Eur. J. , vol.16 , pp. 9758-9762
- Mendoza, A.¹ Pardo, P.² Rodríguez, F.³ Fañanás, F.⁴

57
- 35148890884
- T. W. Schultz, J. W. Yarbrough, R. S. Hunter, A. O. Aptula, Chem. Res. Toxicol. 2007, 20, 1359-1363
- (2007) Chem. Res. Toxicol. , vol.20 , pp. 1359-1363
- Schultz, T.W.¹ Yarbrough, J.W.² Hunter, R.S.³ Aptula, A.O.⁴

58
- 29944436945
- V. Rauhala, K. Nättinen, K. Rissanen, A. M. P. Koskinen, Eur. J. Org. Chem. 2005, 19, 4119-4126
- (2005) Eur. J. Org. Chem. , vol.19 , pp. 4119-4126
- Rauhala, V.¹ Nättinen, K.² Rissanen, K.³ Koskinen, A.M.P.⁴

59
- 4143058102
- L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 10204-10205.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 10204-10205
- Zhang, L.¹ Kozmin, S.A.²

60
- 64249086360
- K. P. Kalbarczyk, S. T. Diver, J. Org. Chem. 2009, 74, 2193-2196.
- (2009) J. Org. Chem. , vol.74 , pp. 2193-2196
- Kalbarczyk, K.P.¹ Diver, S.T.²

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