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Volumn 353, Issue 18, 2011, Pages 3335-3339

Construction of 1,2,5-tricarbonyl compounds using methyl cyanoacetate as a glyoxylate anion synthon combined with copper(I) iodide-catalyzed aerobic oxidation

(3) Kim, Se Hee a Kim, Ko Hoon a Kim, Jae Nyoung a

a Chonnam National University (South Korea)

Author keywords

1,2,5 tricarbonyl compounds; aerobic oxidation; copper(I) iodide; glyoxylate anion synthon; methyl cyanoacetate; umpolung

Indexed keywords

EID: 84255162205 PISSN: 16154150 EISSN: 16154169 Source Type: Journal
DOI: 10.1002/adsc.201100431 Document Type: Article

Times cited : (27)

References (57)

1
- 79251581914
- C. Dresen, M. Richter, M. Pohl, S. Ludeke, M. Muller, Angew. Chem. 2010, 122, 6750-6753
- (2010) Angew. Chem. , vol.122 , pp. 6750-6753
- Dresen, C.¹ Richter, M.² Pohl, M.³ Ludeke, S.⁴ Muller, M.⁵

2
- 77956506031
- Angew. Chem. Int. Ed. 2010, 49, 6600-6603
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 6600-6603

3
- 50849123744
- D. Enders, J. Han, A. Henseler, Chem. Commun. 2008, 3989-3991
- (2008) Chem. Commun. , pp. 3989-3991
- Enders, D.¹ Han, J.² Henseler, A.³

4
- 33746334180
- A. E. Mattson, A. R. Bharadwaj, A. M. Zuhl, K. A. Scheidt, J. Org. Chem. 2006, 71, 5715-5724
- (2006) J. Org. Chem. , vol.71 , pp. 5715-5724
- Mattson, A.E.¹ Bharadwaj, A.R.² Zuhl, A.M.³ Scheidt, K.A.⁴

5
- 1542375011
- A. E. Mattson, A. R. Bharadwaj, K. A. Scheidt, J. Am. Chem. Soc. 2004, 126, 2314-2315
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 2314-2315
- Mattson, A.E.¹ Bharadwaj, A.R.² Scheidt, K.A.³

6
- 27144548436
- M. C. Myers, A. R. Bharadwaj, B. C. Milgram, K. A. Scheidt, J. Am. Chem. Soc. 2005, 127, 14675-14680
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 14675-14680
- Myers, M.C.¹ Bharadwaj, A.R.² Milgram, B.C.³ Scheidt, K.A.⁴

7
- 33746944955
- G. Blay, I. Fernandez, B. Monje, M. C. Munoz, J. R. Pedro, C. Vila, Tetrahedron 2006, 62, 9174-9182
- (2006) Tetrahedron , vol.62 , pp. 9174-9182
- Blay, G.¹ Fernandez, I.² Monje, B.³ Munoz, M.C.⁴ Pedro, J.R.⁵ Vila, C.⁶

8
- 0041567641
- J. E. McMurry, J. Melton, J. Org. Chem. 1973, 38, 4367-4373
- (1973) J. Org. Chem. , vol.38 , pp. 4367-4373
- McMurry, J.E.¹ Melton, J.²

9
- 0000332553
- S. C. Welch, S. Chayabunjonglerd, J. Am. Chem. Soc. 1979, 101, 6768-6769.
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 6768-6769
- Welch, S.C.¹ Chayabunjonglerd, S.²

10
- 0001300938
- H. Stetter, Angew. Chem. 1976, 88, 695-704
- (1976) Angew. Chem. , vol.88 , pp. 695-704
- Stetter, H.¹

11
- 84982417601
- Angew. Chem. Int. Ed. Engl. 1976, 15, 639-647
- (1976) Angew. Chem. Int. Ed. Engl. , vol.15 , pp. 639-647

12
- 0001728892
- D. Seebach, Angew. Chem. 1979, 91, 259-278
- (1979) Angew. Chem. , vol.91 , pp. 259-278
- Seebach, D.¹

13
- 0018454939
- Angew. Chem. Int. Ed. Engl. 1979, 18, 239-258
- (1979) Angew. Chem. Int. Ed. Engl. , vol.18 , pp. 239-258

14
- 77956899292
- J. R. deAlaniz, T. Rovis, Synlett 2009, 1189-1207
- (2009) Synlett , pp. 1189-1207
- Dealaniz, J.R.¹ Rovis, T.²

15
- 38349109278
- D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606-5655.
- (2007) Chem. Rev. , vol.107 , pp. 5606-5655
- Enders, D.¹ Niemeier, O.² Henseler, A.³

16
- 0009622847
- M. T. Reetz, H. Heimbach, K. Schwellnus, Tetrahedron Lett. 1984, 25, 511-514
- (1984) Tetrahedron Lett. , vol.25 , pp. 511-514
- Reetz, M.T.¹ Heimbach, H.² Schwellnus, K.³

17
- 0012937425
- R. J. Cregge, J. L. Herrmann, J. E. Richman, R. F. Romanet, R. H. Schlessinger, Tetrahedron Lett. 1973, 2595-2598
- (1973) Tetrahedron Lett. , pp. 2595-2598
- Cregge, R.J.¹ Herrmann, J.L.² Richman, J.E.³ Romanet, R.F.⁴ Schlessinger, R.H.⁵

18
- 0022981961
- A. Flores-Parra, F. Khuong-Huu, Tetrahedron 1986, 42, 5925-5930
- (1986) Tetrahedron , vol.42 , pp. 5925-5930
- Flores-Parra, A.¹ Khuong-Huu, F.²

19
- 85049058247
- 2-catalyzed aerobic deacylation, which is closely related to our approach, see
- 2-catalyzed aerobic deacylation, which is closely related to our approach, see
- (1997) Tetrahedron Lett. , vol.38 , pp. 4765-4768
- Bestman, H.J.¹ Grob, A.²

20
- 79955596607
- 2 balloon atmosphere showed no reaction.
- 2 balloon atmosphere showed no reaction.
- (2011) Org. Lett. , vol.13 , pp. 2426-2429
- Steward, K.M.¹ Johnson, J.S.²

21
- 54849157500
- D. Enders, M. H. Bonten, G. Raabe, Angew. Chem. 2007, 119, 2364-2367
- (2007) Angew. Chem. , vol.119 , pp. 2364-2367
- Enders, D.¹ Bonten, M.H.² Raabe, G.³

22
- 34250374484
- Angew. Chem. Int. Ed. 2007, 46, 2314-2316
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 2314-2316

23
- 54849432201
- Q. Liu, S. Perreault, T. Rovis, J. Am. Chem. Soc. 2008, 130, 14066-14067
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14066-14067
- Liu, Q.¹ Perreault, S.² Rovis, T.³

24
- 67649506357
- Q. Liu, T. Rovis, Org. Lett. 2009, 11, 2856-2859
- (2009) Org. Lett. , vol.11 , pp. 2856-2859
- Liu, Q.¹ Rovis, T.²

25
- 14544281113
- H. Stetter, H. Skobel, Chem. Ber. 1987, 120, 643-645.
- (1987) Chem. Ber. , vol.120 , pp. 643-645
- Stetter, H.¹ Skobel, H.²

26
- 0000166894
- J. Wennerberg, M. Polla, T. Frejd, J. Org. Chem. 1997, 62, 8735-8740
- (1997) J. Org. Chem. , vol.62 , pp. 8735-8740
- Wennerberg, J.¹ Polla, M.² Frejd, T.³

27
- 0037458890
- R. D. Viirre, R. H. E. Hudson, J. Org. Chem. 2003, 68, 1630-1632
- (2003) J. Org. Chem. , vol.68 , pp. 1630-1632
- Viirre, R.D.¹ Hudson, R.H.E.²

28
- 77954117971
- 1H NMR with the remainder its polymeric form.
- 1H NMR with the remainder its polymeric form.
- (2010) Org. Lett. , vol.12 , pp. 2966-2969
- Urushima, T.¹ Yasui, Y.² Ishikawa, H.³ Hayashi, Y.⁴

29
- 33845552025
- S. S. Kulp, M. J. McGee, J. Org. Chem. 1983, 48, 4097-4098
- (1983) J. Org. Chem. , vol.48 , pp. 4097-4098
- Kulp, S.S.¹ McGee, M.J.²

30
- 0019193201
- K. A. Parker, J. Kallmerten, J. Org. Chem. 1980, 45, 2614-2620
- (1980) J. Org. Chem. , vol.45 , pp. 2614-2620
- Parker, K.A.¹ Kallmerten, J.²

31
- 33847802830
- S. J. Selikson, D. S. Watt, J. Org. Chem. 1975, 40, 267-268
- (1975) J. Org. Chem. , vol.40 , pp. 267-268
- Selikson, S.J.¹ Watt, D.S.²

32
- 0000947717
- R. W. Freerksen, S. J. Selikson, R. R. Wroble, K. S. Kyler, D. S. Watt, J. Org. Chem. 1983, 48, 4087-4096
- (1983) J. Org. Chem. , vol.48 , pp. 4087-4096
- Freerksen, R.W.¹ Selikson, S.J.² Wroble, R.R.³ Kyler, K.S.⁴ Watt, D.S.⁵

33
- 0006987160
- D. S. Watt, J. Org. Chem. 1974, 39, 2799-2800
- (1974) J. Org. Chem. , vol.39 , pp. 2799-2800
- Watt, D.S.¹

34
- 0026040506
- S. Adam, Tetrahedron 1991, 47, 7609-7614
- (1991) Tetrahedron , vol.47 , pp. 7609-7614
- Adam, S.¹

35
- 78049388019
- S. H. Kim, S. Lee, H. S. Lee, J. N. Kim, Tetrahedron Lett. 2010, 51, 6305-6309.
- (2010) Tetrahedron Lett. , vol.51 , pp. 6305-6309
- Kim, S.H.¹ Lee, S.² Lee, H.S.³ Kim, J.N.⁴

36
- 0000926052
- H. A. P. de Jongh, C. R. H. I. de Jonge, H. J. M. Sinnige, W. J. de Klein, W. G. B. Huysmans, W. J. Mijs, W. J. van den Hoek, J. Smidt, J. Org. Chem. 1972, 37, 1960-1966
- (1972) J. Org. Chem. , vol.37 , pp. 1960-1966
- De Jongh, H.A.P.¹ De Jonge, C.R.H.I.² Sinnige, H.J.M.³ De Klein, W.J.⁴ Huysmans, W.G.B.⁵ Mijs, W.J.⁶ Hoek, W.J.V.D.⁷ Smidt, J.⁸

37
- 0000561755
- H. A. P. de Jongh, C. R. H. I. de Jonge, W. J. Mijs, J. Org. Chem. 1971, 36, 3160-3168
- (1971) J. Org. Chem. , vol.36 , pp. 3160-3168
- De Jongh, H.A.P.¹ De Jonge, C.R.H.I.² Mijs, W.J.³

38
- 27944487943
- M. C. Kozlowski, E. S. DiVirgilio, K. Malolanarasimhan, C. A. Mulrooney, Tetrahedron: Asymmetry 2005, 16, 3599-3605.
- (2005) Tetrahedron: Asymmetry , vol.16 , pp. 3599-3605
- Kozlowski, M.C.¹ Divirgilio, E.S.² Malolanarasimhan, K.³ Mulrooney, C.A.⁴

39
- 17844369704
- J. Zhu, H. Wong, Z. Zhang, Z. Yin, J. F. Kadow, N. A. Meanwell, T. Wang, Tetrahedron Lett. 2005, 46, 3587-3589
- (2005) Tetrahedron Lett. , vol.46 , pp. 3587-3589
- Zhu, J.¹ Wong, H.² Zhang, Z.³ Yin, Z.⁴ Kadow, J.F.⁵ Meanwell, N.A.⁶ Wang, T.⁷

40
- 0041374164
- Z. Yang, Z. Zhang, N. A. Meanwell, J. F. Kadow, T. Wang, Org. Lett. 2002, 4, 1103-1105
- (2002) Org. Lett. , vol.4 , pp. 1103-1105
- Yang, Z.¹ Zhang, Z.² Meanwell, N.A.³ Kadow, J.F.⁴ Wang, T.⁵

41
- 0041402101
- K. Takahashi, K. Shibasaki, K. Ogura, H. Iida, Chem. Lett. 1983, 859-862.
- (1983) Chem. Lett. , pp. 859-862
- Takahashi, K.¹ Shibasaki, K.² Ogura, K.³ Iida, H.⁴

42
- 52049121268
- M. R. Saidi, N. Azizi, E. Akbari, F. Ebrahimi, J. Mol. Catal. A: Chem. 2008, 292, 44-48
- (2008) J. Mol. Catal. A: Chem. , vol.292 , pp. 44-48
- Saidi, M.R.¹ Azizi, N.² Akbari, E.³ Ebrahimi, F.⁴

43
- 33846573334
- M. Meciarova, S. Toma, Chem. Eur. J. 2007, 13, 1268-1272
- (2007) Chem. Eur. J. , vol.13 , pp. 1268-1272
- Meciarova, M.¹ Toma, S.²

44
- 73049113992
- S. H. Kim, H. S. Lee, K. H. Kim, J. N. Kim, Tetrahedron Lett. 2009, 50, 6476-6479
- (2009) Tetrahedron Lett. , vol.50 , pp. 6476-6479
- Kim, S.H.¹ Lee, H.S.² Kim, K.H.³ Kim, J.N.⁴

45
- 3042784995
- N. Selvakumar, G. G. Rajulu, J. Org. Chem. 2004, 69, 4429-4432
- (2004) J. Org. Chem. , vol.69 , pp. 4429-4432
- Selvakumar, N.¹ Rajulu, G.G.²

46
- 0142026581
- J. You, J. G. Verkade, J. Org. Chem. 2003, 68, 8003-8007
- (2003) J. Org. Chem. , vol.68 , pp. 8003-8007
- You, J.¹ Verkade, J.G.²

47
- 0042912889
- C. Gao, X. Tao, Y. Qian, J. Huang, Synlett 2003, 1716-1718
- (2003) Synlett , pp. 1716-1718
- Gao, C.¹ Tao, X.² Qian, Y.³ Huang, J.⁴

48
- 77951003571
- E. J. Park, S. Lee, S. Chang, J. Org. Chem. 2010, 75, 2760-2762
- (2010) J. Org. Chem. , vol.75 , pp. 2760-2762
- Park, E.J.¹ Lee, S.² Chang, S.³

49
- 56949086445
- For further references on the synthesis of starting materials, see the Supporting Information.
- J. K. Augustine, Y. A. Naik, V. Vairaperumal, S. Narasimhan, Tetrahedron 2009, 65, 134-138. For further references on the synthesis of starting materials, see the Supporting Information.
- (2009) Tetrahedron , vol.65 , pp. 134-138
- Augustine, J.K.¹ Naik, Y.A.² Vairaperumal, V.³ Narasimhan, S.⁴

50
- 77955143819
- R.-L. Yan, J. Luo, C.-X. Wang, C.-W. Ma, G.-S. Huang, Y.-M. Liang, J. Org. Chem. 2010, 75, 5395-5397.
- (2010) J. Org. Chem. , vol.75 , pp. 5395-5397
- Yan, R.-L.¹ Luo, J.² Wang, C.-X.³ Ma, C.-W.⁴ Huang, G.-S.⁵ Liang, Y.-M.⁶

51
- 33947294845
- N. Rabjohn, C. A. Harbert, J. Org. Chem. 1970, 35, 3240-3243
- (1970) J. Org. Chem. , vol.35 , pp. 3240-3243
- Rabjohn, N.¹ Harbert, C.A.²

52
- 0034619129
- Y. Matsubara, T. Matsuda, A. Kato, Y. Yamaguchi, Z.-i. Yoshida, Tetrahedron Lett. 2000, 41, 7901-7904
- (2000) Tetrahedron Lett. , vol.41 , pp. 7901-7904
- Matsubara, Y.¹ Matsuda, T.² Kato, A.³ Yamaguchi, Y.⁴ Yoshida, Z.-I.⁵

53
- 0027765777
- For a similar Cu-mediated deacylative oxidation, see
- D. T. Breslin, M. A. Fox, J. Am. Chem. Soc. 1993, 115, 11716-11721. For a similar Cu-mediated deacylative oxidation, see
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 11716-11721
- Breslin, D.T.¹ Fox, M.A.²

54
- 0028040750
- J. Cossy, D. Belotti, V. Bellosta, D. Brocca, Tetrahedron Lett. 1994, 35, 6089-6092.
- (1994) Tetrahedron Lett. , vol.35 , pp. 6089-6092
- Cossy, J.¹ Belotti, D.² Bellosta, V.³ Brocca, D.⁴

55
- 61649123389
- S. Zhao, Y. Ren, J. Wang, W. Yin, J. Phys. Chem. A 2009, 113, 1075-1085
- (2009) J. Phys. Chem. A , vol.113 , pp. 1075-1085
- Zhao, S.¹ Ren, Y.² Wang, J.³ Yin, W.⁴

56
- 33748515907
- M. A. S. Goher, F. A. Mautner, J. Chem. Soc. Dalton Trans. 1999, 1923-1924
- (1999) J. Chem. Soc. Dalton Trans. , pp. 1923-1924
- Goher, M.A.S.¹ Mautner, F.A.²

57
- 0034643407
- A. Luna, B. Amekraz, J. P. Morizur, J. Tortajada, O. Mo, M. Yanez, J. Phys. Chem. A 2000, 104, 3132-3141.
- (2000) J. Phys. Chem. A , vol.104 , pp. 3132-3141
- Luna, A.¹ Amekraz, B.² Morizur, J.P.³ Tortajada, J.⁴ Mo, O.⁵ Yanez, M.⁶

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