SCOPUS 정보 검색 플랫폼

Volumn 46, Issue 47, 2010, Pages 9064-9066

Pd-catalyzed 5-endo-trig-type cyclization of β,γ-unsaturated carbonyl compounds: An efficient ring closing reaction to give γ-butenolides and 3-pyrrolin-2-ones

(7) Bajracharya, Gan B a Koranne, Priti S a Nadaf, Rashid N a Gabr, Randa Kassem Mohamed a Takenaka, Kazuhiro a Takizawa, Shinobu a Sasai, Hiroaki a

a OSAKA UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BUTENOLIDE; CARBONYL DERIVATIVE; PALLADIUM; PYRROLINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS;

EID: 78649388118 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/c0cc02352c Document Type: Article

Times cited : (35)

References (62)

1
- 63149164850
- G. B. Bajracharya M. A. Arai P. S. Koranne T. Suzuki S. Takizawa H. Sasai Bull. Chem. Soc. Jpn. 2009 82 285
- (2009) Bull. Chem. Soc. Jpn. , vol.82 , pp. 285
- Bajracharya, G.B.¹ Arai, M.A.² Koranne, P.S.³ Suzuki, T.⁴ Takizawa, S.⁵ Sasai, H.⁶

2
- 68249145558
- T. Tsujihara K. Takenaka K. Onitsuka M. Hatanaka H. Sasai J. Am. Chem. Soc. 2009 131 3452
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 3452
- Tsujihara, T.¹ Takenaka, K.² Onitsuka, K.³ Hatanaka, M.⁴ Sasai, H.⁵

3
- 73149098957
- T. Tsujihara T. Shinohara K. Takenaka S. Takizawa K. Onitsuka M. Hatanaka H. Sasai J. Org. Chem. 2009 74 9274
- (2009) J. Org. Chem. , vol.74 , pp. 9274
- Tsujihara, T.¹ Shinohara, T.² Takenaka, K.³ Takizawa, S.⁴ Onitsuka, K.⁵ Hatanaka, M.⁶ Sasai, H.⁷

4
- 77955128212
- K. Takenaka Y. Tanigaki M. L. Patil C. V. L. Rao S. Takizawa T. Suzuki H. Sasai Tetrahedron: Asymmetry 2010 21 767
- (2010) Tetrahedron: Asymmetry , vol.21 , pp. 767
- Takenaka, K.¹ Tanigaki, Y.² Patil, M.L.³ Rao, C.V.L.⁴ Takizawa, S.⁵ Suzuki, T.⁶ Sasai, H.⁷

5
- 77955153981
- For recent reports on the 5-endo-trig radical cyclizations:
- K. Takenaka S. C. Mohanta M. L. Patil C. V. L. Rao S. Takizawa T. Suzuki H. Sasai Org. Lett. 2010 12 3480
- (2010) Org. Lett. , vol.12 , pp. 3480
- Takenaka, K.¹ Mohanta, S.C.² Patil, M.L.³ Rao, C.V.L.⁴ Takizawa, S.⁵ Suzuki, T.⁶ Sasai, H.⁷

6
- 33749992947
- M. J. Palframan K. Tchabanenko J. Robertson Tetrahedron Lett. 2006 47 8423
- (2006) Tetrahedron Lett. , vol.47 , pp. 8423
- Palframan, M.J.¹ Tchabanenko, K.² Robertson, J.³

7
- 34648832258
- K. Takeuchi A. Ishita J.-i. Matsuo H. Ishibashi Tetrahedron 2007 63 11101
- (2007) Tetrahedron , vol.63 , pp. 11101
- Takeuchi, K.¹ Ishita, A.² M. J, -I.³ Ishibashi, H.⁴

8
- 50449103168
- I. V. Alabugin K. Gilmore S. Patil M. Manoharan S. V. Kovalenko R. J. Clark I. Ghiviriga J. Am. Chem. Soc. 2008 130 11535
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 11535
- Alabugin, I.V.¹ Gilmore, K.² Patil, S.³ Manoharan, M.⁴ Kovalenko, S.V.⁵ Clark, R.J.⁶ Ghiviriga, I.⁷

9
- 44449098749
- For recent reports on the 5-endo-trig cyclizations of certain fluorous compounds:
- S. Bogen J.-P. Goddard L. Fensterbank M. Malacria ARKIVOC 2008 viii 126
- (2008) ARKIVOC , vol.8 , pp. 126
- Bogen, S.¹ Goddard, J.-P.² Fensterbank, L.³ Malacria, M.⁴

10
- 54849439820
- For recent reports on the 5-endo-trig ionic cyclizations:
- J. Ichikawa Y. Iwai R. Nadano T. Mori M. Ikeda Chem.-Asian J. 2008 3 393
- (2008) Chem.-Asian J. , vol.3 , pp. 393
- Ichikawa, J.¹ Iwai, Y.² Nadano, R.³ Mori, T.⁴ Ikeda, M.⁵

11
- 33746935596
- A. D. Jones A. L. Redfern D. W. Knight I. R. Morgan A. C. Williams Tetrahedron 2006 62 9247
- (2006) Tetrahedron , vol.62 , pp. 9247
- Jones, A.D.¹ Redfern, A.L.² Knight, D.W.³ Morgan, I.R.⁴ Williams, A.C.⁵

12
- 33644640549
- J. E. Kropf I. C. Meigh M. W. P. Bebbington S. M. Weinreb J. Org. Chem. 2006 71 2046
- (2006) J. Org. Chem. , vol.71 , pp. 2046
- Kropf, J.E.¹ Meigh, I.C.² Bebbington, M.W.P.³ Weinreb, S.M.⁴

13
- 33644934691
- H. Ohno Y. Kadoh N. Fujii T. Tanaka Org. Lett. 2006 8 947
- (2006) Org. Lett. , vol.8 , pp. 947
- Ohno, H.¹ Kadoh, Y.² Fujii, N.³ Tanaka, T.⁴

14
- 34147191957
- J. J. Caldwell D. Craig S. P. East ARKIVOC 2007 xii 67
- (2007) ARKIVOC , vol.12 , pp. 67
- Caldwell, J.J.¹ Craig, D.² East, S.P.³

15
- 33744938666
- N. S. Karanjule S. D. Markad V. S. Shinde D. D. Dhavale J. Org. Chem. 2006 71 4667
- (2006) J. Org. Chem. , vol.71 , pp. 4667
- Karanjule, N.S.¹ Markad, S.D.² Shinde, V.S.³ Dhavale, D.D.⁴

16
- 33751262964
- P. Vital P.-O. Norrby D. Tanner Synlett 2006 3140
- (2006) Synlett , pp. 3140
- Vital, P.¹ Norrby, P.-O.² Tanner, D.³

17
- 35148886692
- D. Ray S. Paul S. Brahma J. K. Ray Tetrahedron Lett. 2007 48 8005
- (2007) Tetrahedron Lett. , vol.48 , pp. 8005
- Ray, D.¹ Paul, S.² Brahma, S.³ Ray, J.K.⁴

18
- 40249107470
- A. M. Zawisza B. Ganchegui I. Gonzalez S. Bouquillon A. Roglans F. Henin J. Muzart J. Mol. Catal. A: Chem. 2008 283 140
- (2008) J. Mol. Catal. A: Chem. , vol.283 , pp. 140
- Zawisza, A.M.¹ Ganchegui, B.² Gonzalez, I.³ Bouquillon, S.⁴ Roglans, A.⁵ Henin, F.⁶ Muzart, J.⁷

19
- 44449121406
- Y.-C. Wu M. Liron J. Zhu J. Am. Chem. Soc. 2008 130 7148
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 7148
- Wu, Y.-C.¹ Liron, M.² Zhu, J.³

20
- 58149314193
- H. Fuwa M. Sasaki J. Org. Chem. 2009 74 212
- (2009) J. Org. Chem. , vol.74 , pp. 212
- Fuwa, H.¹ Sasaki, M.²

21
- 58149345462
- J. Maruyama H. Yamashita T. Watanabe S. Arai A. Nishida Tetrahedron 2009 65 1327
- (2009) Tetrahedron , vol.65 , pp. 1327
- Maruyama, J.¹ Yamashita, H.² Watanabe, T.³ Arai, S.⁴ Nishida, A.⁵

22
- 0000987717
- B. Figadere Acc. Chem. Res. 1995 28 359
- (1995) Acc. Chem. Res. , vol.28 , pp. 359
- Figadere, B.¹

23
- 0032891112
- F. Q. Alali X.-X. Liu J. L. McLaughlin J. Nat. Prod. 1999 62 504
- (1999) J. Nat. Prod. , vol.62 , pp. 504
- Alali, F.Q.¹ Liu, X.-X.² McLaughlin, J.L.³

24
- 0033960326
- C. J. Smith D. Abbanat V. S. Bernan W. M. Maiese M. Greenstein J. Jompa A. Tahir C. M. Ireland J. Nat. Prod. 2000 63 142
- (2000) J. Nat. Prod. , vol.63 , pp. 142
- Smith, C.J.¹ Abbanat, D.² Bernan, V.S.³ Maiese, W.M.⁴ Greenstein, M.⁵ Jompa, J.⁶ Tahir, A.⁷ Ireland, C.M.⁸

25
- 3142694085
- M. F. Brana M. L. Garcia B. Lopez B. de Pascual-Teresa A. Ramos J. M. Pozuelo M. T. Dominguez Org. Biomol. Chem. 2004 2 1864
- (2004) Org. Biomol. Chem. , vol.2 , pp. 1864
- Brana, M.F.¹ Garcia, M.L.² Lopez, B.³ De Pascual-Teresa, B.⁴ Ramos, A.⁵ Pozuelo, J.M.⁶ Dominguez, M.T.⁷

26
- 21444434074
- R. T. Li Q. B. Han Y. T. Zheng R. R. Wang L. M. Yang Y. Lu S. Q. Sang Q. T. Zheng Q. S. Zhao H. D. Sun Chem. Commun. 2005 2936
- (2005) Chem. Commun. , pp. 2936
- Li, R.T.¹ Han, Q.B.² Zheng, Y.T.³ Wang, R.R.⁴ Yang, L.M.⁵ Lu, Y.⁶ Sang, S.Q.⁷ Zheng, Q.T.⁸ Zhao, Q.S.⁹ Sun, H.D.¹⁰

27
- 55449117295
- For selected reports on synthesis of racemic form:
- L. Tu Y. Zhao Z. Yu Y. Cong G. Xu L. Peng P. Zhang X. Cheng Q. Zhao Helv. Chim. Acta 2008 91 1578
- (2008) Helv. Chim. Acta , vol.91 , pp. 1578
- Tu, L.¹ Zhao, Y.² Yu, Z.³ Cong, Y.⁴ Xu, G.⁵ Peng, L.⁶ Zhang, P.⁷ Cheng, X.⁸ Zhao, Q.⁹

28
- 49149133142
- F. W. Machado-Araujo J. Gore Tetrahedron Lett. 1981 22 1969
- (1981) Tetrahedron Lett. , vol.22 , pp. 1969
- MacHado-Araujo, F.W.¹ Gore, J.²

29
- 0001432309
- I. Kuwajima H. Urabe Tetrahedron Lett. 1981 22 5191
- (1981) Tetrahedron Lett. , vol.22 , pp. 5191
- Kuwajima, I.¹ Urabe, H.²

30
- 0000066571
- A. Pelter M. Rowlands Tetrahedron Lett. 1987 28 1203
- (1987) Tetrahedron Lett. , vol.28 , pp. 1203
- Pelter, A.¹ Rowlands, M.²

31
- 0001613006
- E. Yoneda T. Kaneko S. Zhang K. Onitsuka S. Takahashi Org. Lett. 2000 2 441
- (2000) Org. Lett. , vol.2 , pp. 441
- Yoneda, E.¹ Kaneko, T.² Zhang, S.³ Onitsuka, K.⁴ Takahashi, S.⁵

32
- 18844454773
- M. Bassetti A. D'Annibale A. Fanfoni F. Minissi Org. Lett. 2005 7 1805
- (2005) Org. Lett. , vol.7 , pp. 1805
- Bassetti, M.¹ D'Annibale, A.² Fanfoni, A.³ Minissi, F.⁴

33
- 65549115427
- J. S. Yadav B. V. S. Reddy G. Narasimhulu N. S. Reddy P. J. Reddy Tetrahedron Lett. 2009 50 3760
- (2009) Tetrahedron Lett. , vol.50 , pp. 3760
- Yadav, J.S.¹ Reddy, B.V.S.² Narasimhulu, G.³ Reddy, N.S.⁴ Reddy, P.J.⁵

34
- 0028955801
- Q.-H. Chen Z. Geng B. Huang Tetrahedron: Asymmetry 1995 6 401
- (1995) Tetrahedron: Asymmetry , vol.6 , pp. 401
- Chen, Q.-H.¹ Geng, Z.² Huang, B.³

35
- 0000902857
- S. Tsuboi J. Sakamoto H. Yamashita T. Sakai M. Utaka J. Org. Chem. 1998 63 1102
- (1998) J. Org. Chem. , vol.63 , pp. 1102
- Tsuboi, S.¹ Sakamoto, J.² Yamashita, H.³ Sakai, T.⁴ Utaka, M.⁵

36
- 0033605028
- M. Tiecco L. Testaferri F. Marini C. Santi L. Bagnoli A. Temperini Tetrahedron: Asymmetry 1999 10 747
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 747
- Tiecco, M.¹ Testaferri, L.² Marini, F.³ Santi, C.⁴ Bagnoli, L.⁵ Temperini, A.⁶

37
- 0035910844
- S. Ma Z. Shi S. Wu Tetrahedron: Asymmetry 2001 12 193
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 193
- Ma, S.¹ Shi, Z.² Wu, S.³

38
- 0037419866
- S. P. Brown N. C. Goodwin D. W. C. MacMillan J. Am. Chem. Soc. 2003 125 1192
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 1192
- Brown, S.P.¹ Goodwin, N.C.² MacMillan, D.W.C.³

39
- 33751012442
- E. L. Carswell M. L. Snapper A. H. Hoveyda Angew. Chem., Int. Ed. 2006 45 7230
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 7230
- Carswell, E.L.¹ Snapper, M.L.² Hoveyda, A.H.³

40
- 52649127410
- A. Yamaguchi S. Matsunaga M. Shibasaki Org. Lett. 2008 10 2319
- (2008) Org. Lett. , vol.10 , pp. 2319
- Yamaguchi, A.¹ Matsunaga, S.² Shibasaki, M.³

41
- 44949204654
- Y.-Q. Jiang Y.-L. Shi M. Shi J. Am. Chem. Soc. 2008 130 7202
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 7202
- Jiang, Y.-Q.¹ Shi, Y.-L.² Shi, M.³

42
- 0001406164
- D. Goldsmith D. Liotta C. Lee G. Zima Tetrahedron Lett. 1979 20 4801
- (1979) Tetrahedron Lett. , vol.20 , pp. 4801
- Goldsmith, D.¹ Liotta, D.² Lee, C.³ Zima, G.⁴

43
- 0033524784
- F. Bravo M. Kassou S. Castillon Tetrahedron Lett. 1999 40 1187
- (1999) Tetrahedron Lett. , vol.40 , pp. 1187
- Bravo, F.¹ Kassou, M.² Castillon, S.³

44
- 0000163555
- M. Tiecco L. Testaferri F. Marini S. Sternativo L. Bagnoli C. Santi A. Temperini Tetrahedron: Asymmetry 2001 12 1493
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 1493
- Tiecco, M.¹ Testaferri, L.² Marini, F.³ Sternativo, S.⁴ Bagnoli, L.⁵ Santi, C.⁶ Temperini, A.⁷

45
- 34447542393
- J. M. Garnier S. Robin G. Rousseau Eur. J. Org. Chem. 2007 3281
- (2007) Eur. J. Org. Chem. , pp. 3281
- Garnier, J.M.¹ Robin, S.² Rousseau, G.³

46
- 34547944988
- D. M. Browne O. Niyomura T. Wirth Org. Lett. 2007 9 3169
- (2007) Org. Lett. , vol.9 , pp. 3169
- Browne, D.M.¹ Niyomura, O.² Wirth, T.³

47
- 0000682634
- 3 (dba = dibenzylideneacetone), was found to be a poor catalyst 3-Pyrrolin-2-ones are important synthons to prepare a variety of biologically active compounds;
- A. Kasahara T. Izumi K. Sato M. Maemura T. Hayasaka Bull. Chem. Soc. Jpn. 1977 50 1899
- (1977) Bull. Chem. Soc. Jpn. , vol.50 , pp. 1899
- Kasahara, A.¹ Izumi, T.² Sato, K.³ Maemura, M.⁴ Hayasaka, T.⁵

48
- 37049082507
- P. Jouin B. Castro J. Chem. Soc., Perkin Trans. 1 1987 1177
- (1987) J. Chem. Soc., Perkin Trans. 1 , pp. 1177
- Jouin, P.¹ Castro, B.²

49
- 0345225165
- W. J. Klaver H. Hiemstra W. N. Speckamp J. Am. Chem. Soc. 1989 111 2588
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 2588
- Klaver, W.J.¹ Hiemstra, H.² Speckamp, W.N.³

50
- 0028049116
- D. Griffart-Brunet N. Langois Tetrahedron Lett. 1994 35 119
- (1994) Tetrahedron Lett. , vol.35 , pp. 119
- Griffart-Brunet, D.¹ Langois, N.²

51
- 0000011101
- G. Casiraghi P. Spanu G. Rassu L. Pinna F. Ulgheri J. Org. Chem. 1994 59 2906
- (1994) J. Org. Chem. , vol.59 , pp. 2906
- Casiraghi, G.¹ Spanu, P.² Rassu, G.³ Pinna, L.⁴ Ulgheri, F.⁵

52
- 0028343931
- N. J. Newcombe F. Ya R. J. Vijn H. Hiemstra W. N. Speckamp J. Chem. Soc., Chem. Commun. 1994 767
- (1994) J. Chem. Soc., Chem. Commun. , pp. 767
- Newcombe, N.J.¹ Ya, F.² Vijn, R.J.³ Hiemstra, H.⁴ Speckamp, W.N.⁵

53
- 0028077856
- S. Paik S. Carmeli J. Cullingham R. E. Moore G. M. L. Patterson M. A. Tius J. Am. Chem. Soc. 1994 116 8116
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 8116
- Paik, S.¹ Carmeli, S.² Cullingham, J.³ Moore, R.E.⁴ Patterson, G.M.L.⁵ Tius, M.A.⁶

54
- 0030208487
- D. Ma J. Ma W. Ding L. Dai Tetrahedron: Asymmetry 1996 7 2365
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 2365
- Ma, D.¹ Ma, J.² Ding, W.³ Dai, L.⁴

55
- 3142657150
- G. Verniest S. Boterberg F. Bombeke C. V. Stevens N. D. Kimpe Synlett 2004 1059
- (2004) Synlett , pp. 1059
- Verniest, G.¹ Boterberg, S.² Bombeke, F.³ Stevens, C.V.⁴ Kimpe, N.D.⁵

56
- 2442454610
- The phenylsulfonyl protecting group gave a similar result as compared with 7c. In contrast, the p-chlorophenylsulfonyl, the benzyl substituted, and the unprotected enamide failed to react. See the ESI for details
- R. Naitoh Y. Nakamura E. Katano Y. Nakamura E. Okada M. Asaoka Heterocycles 2004 63 1009
- (2004) Heterocycles , vol.63 , pp. 1009
- Naitoh, R.¹ Nakamura, Y.² Katano, E.³ Nakamura, Y.⁴ Okada, E.⁵ Asaoka, M.⁶

57
- 0038179493
- P. Pinho A. J. Minnaard B. L. Feringa Org. Lett. 2003 5 259
- (2003) Org. Lett. , vol.5 , pp. 259
- Pinho, P.¹ Minnaard, A.J.² Feringa, B.L.³

58
- 29344449953
- R. M. Trend Y. K. Ramtohul B. M. Stoltz J. Am. Chem. Soc. 2005 127 17778
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 17778
- Trend, R.M.¹ Ramtohul, Y.K.² Stoltz, B.M.³

59
- 33845377650
- T. Hosokawa C. Okuda S.-I. Murahashi J. Org. Chem. 1985 50 1282
- (1985) J. Org. Chem. , vol.50 , pp. 1282
- Hosokawa, T.¹ Okuda, C.² Murahashi, S.-I.³

60
- 0033525716
- Y. Uozumi H. Kyota K. Kato M. Ogasawara T. Hayashi J. Org. Chem. 1999 64 1620
- (1999) J. Org. Chem. , vol.64 , pp. 1620
- Uozumi, Y.¹ Kyota, H.² Kato, K.³ Ogasawara, M.⁴ Hayashi, T.⁵

61
- 85008090337
- D. A. Evans K. A. Woerpel M. M. Hinman M. M. Faul J. Am. Chem. Soc. 1991 113 726
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 726
- Evans, D.A.¹ Woerpel, K.A.² Hinman, M.M.³ Faul, M.M.⁴

62
- 85022460851
- When racemic 2a was stirred with optically pure Pd - iPr-SPRIX complex and p-benzoquinone for 24 h, racemic 2a was recovered in >95% yield
- E. J. Corey N. Imai H.-Y. Zhang J. Am. Chem. Soc. 1991 113 728
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 728
- Corey, E.J.¹ Imai, N.² Zhang, H.-Y.³

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