SCOPUS 정보 검색 플랫폼

Chinese Journal of Chemistry

Volumn 26, Issue 4, 2008, Pages 599-601

Metal-free uncatalyzed reduction of α,β-unsaturated ketones mediated by hantzsch 1,4-dihydropyridine

(3) Xu, Hua Jian a Liu, You Cheng a,b Fu, Yao a

a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA (China)

b LANZHOU UNIVERSITY (China)

Author keywords

, unsaturated ketone reduction; Coenzyme NADH model; Hantzsch ester; Mechanism

Indexed keywords

EID: 45249121236 PISSN: 1001604X EISSN: None Source Type: Journal
DOI: 10.1002/cjoc.200890112 Document Type: Article

Times cited : (7)

References (48)

1
- 0000390898
- Eds, Dolphin, D, Poulson, R, Avramovic, O, Wiley-Interscience, New York, Part A, p
- (a) Westheimer, F. H In Pyridine Nucleotide Coenzyme, Eds.: Dolphin, D.; Poulson, R.; Avramovic, O., Wiley-Interscience, New York, 1988, Part A, p. 253.
- (1988) Pyridine Nucleotide Coenzyme , pp. 253
- Westheimer, F.H.I.¹

2
- 0001548808
- (b) Bunting, J. W. Bioorg. Chem. 1991, 19, 456.
- (1991) Bioorg. Chem , vol.19 , pp. 456
- Bunting, J.W.¹

3
- 0000153757
- (c) Murakami, Y.; Kikuchi, J. I.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721.
- (1996) Chem. Rev , vol.96 , pp. 721
- Murakami, Y.¹ Kikuchi, J.I.² Hisaeda, Y.³ Hayashida, O.⁴

4
- 10944220196
- (a) Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 6660.
- (2004) Angew. Chem., Int. Ed , vol.43 , pp. 6660
- Yang, J.W.¹ Hechavarria Fonseca, M.T.² List, B.³

5
- 11244320360
- (b) Yang, J. W.; Hechavarria Fonseca, M. T.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2005, 44, 108.
- (2005) Angew. Chem., Int. Ed , vol.44 , pp. 108
- Yang, J.W.¹ Hechavarria Fonseca, M.T.² Vignola, N.³ List, B.⁴

6
- 20444410116
- (c) Adolfsson, H. Angew. Chem., Int. Ed. 2005, 44, 3340.
- (2005) Angew. Chem., Int. Ed , vol.44 , pp. 3340
- Adolfsson, H.¹

7
- 11844277087
- (d) Ouellet, S. G.; Tuttle, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 32.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 32
- Ouellet, S.G.¹ Tuttle, J.B.² MacMillan, D.W.C.³

8
- 33746286405
- (e) Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193.
- (2006) Angew. Chem., Int. Ed , vol.45 , pp. 4193
- Mayer, S.¹ List, B.²

9
- 33749516633
- (a) Tuttle, J. B.; Ouellet, S. G.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 12662.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 12662
- Tuttle, J.B.¹ Ouellet, S.G.² MacMillan, D.W.C.³

10
- 33750084396
- (b) Martin, N. J. A.; List, B. J. Am. Chem. Soc. 2006, 128, 13368.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 13368
- Martin, N.J.A.¹ List, B.²

11
- 25444480017
- (a) Rueping, M.; Azap, C.; Sugiono, E.; Theissmann, T. Synlett 2005, 2367.
- (2005) Synlett , pp. 2367
- Rueping, M.¹ Azap, C.² Sugiono, E.³ Theissmann, T.⁴

12
- 24044465512
- (b) Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. Org. Lett. 2005, 7, 3781.
- (2005) Org. Lett , vol.7 , pp. 3781
- Rueping, M.¹ Sugiono, E.² Azap, C.³ Theissmann, T.⁴ Bolte, M.⁵

13
- 28044438742
- (c) Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2005, 44, 7424.
- (2005) Angew. Chem., Int. Ed , vol.44 , pp. 7424
- Hoffmann, S.¹ Seayad, A.M.² List, B.³

14
- 33645755227
- (d) Menche, D.; Arikan, F. Synlett 2006, 841.
- (2006) Synlett , pp. 841
- Menche, D.¹ Arikan, F.²

15
- 30744477746
- (e) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 84
- Storer, R.I.¹ Carrera, D.E.² Ni, Y.³ MacMillan, D.W.C.⁴

16
- 33749534513
- (f) Hoffmann, S.; Nicoletti, M.; List, B. J. Am. Chem. Soc. 2006, 128, 13074.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 13074
- Hoffmann, S.¹ Nicoletti, M.² List, B.³

17
- 34250835001
- (g) Zhou, J.; List, B. J. Am. Chem. Soc. 2007, 129, 7498.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 7498
- Zhou, J.¹ List, B.²

18
- 33646574664
- (a) Rueping, M.; Theissmann, T.; Antonchick, A. P. Synlett 2006, 1071.
- (2006) Synlett , pp. 1071
- Rueping, M.¹ Theissmann, T.² Antonchick, A.P.³

19
- 33746269442
- (b) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683.
- (2006) Angew. Chem., Int. Ed , vol.45 , pp. 3683
- Rueping, M.¹ Antonchick, A.P.² Theissmann, T.³

20
- 33750148995
- (c) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 6751.
- (2006) Angew. Chem., Int. Ed , vol.45 , pp. 6751
- Rueping, M.¹ Antonchick, A.P.² Theissmann, T.³

21
- 33845993240
- Yang, J. W.; List, B. Org. Lett. 2006, 8, 5653.
- (2006) Org. Lett , vol.8 , pp. 5653
- Yang, J.W.¹ List, B.²

22
- 34547492913
- Martin, N. J. A.; Ozores, L.; List, B. J. Am. Chem. Soc. 2007, 129, 8976.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 8976
- Martin, N.J.A.¹ Ozores, L.² List, B.³

23
- 0242660859
- Garden, S. J.; Guimarães, C. R. W.; Corréa, B.; Oliveira, C. A. F.; Pinto, A. C.; Alencastro, R. B. J. Org. Chem. 2003, 68, 8815.
- (2003) J. Org. Chem , vol.68 , pp. 8815
- Garden, S.J.¹ Guimarães, C.R.W.² Corréa, B.³ Oliveira, C.A.F.⁴ Pinto, A.C.⁵ Alencastro, R.B.⁶

24
- 0035847184
- Zhu, X. Q.; Wang, H. Y.; Wang, J. S.; Liu, Y. C. J. Org. Chem. 2001, 66, 344.
- (2001) J. Org. Chem , vol.66 , pp. 344
- Zhu, X.Q.¹ Wang, H.Y.² Wang, J.S.³ Liu, Y.C.⁴

25
- 21544440160
- Liu, Z.; Han, B.; Liu, Q.; Zhang, W.; Yang, L.; Liu, Z. L.; Yu, W. Synlett 2005, 1579.
- (2005) Synlett , pp. 1579
- Liu, Z.¹ Han, B.² Liu, Q.³ Zhang, W.⁴ Yang, L.⁵ Liu, Z.L.⁶ Yu, W.⁷

26
- 33644897313
- Liu, Z.; Liu, Q.; Zhang, W.; Mu, R.; Yang, L.; Liu, Z. L.; Yu, W. Synthesis 2006, 771.
- (2006) Synthesis , pp. 771
- Liu, Z.¹ Liu, Q.² Zhang, W.³ Mu, R.⁴ Yang, L.⁵ Liu, Z.L.⁶ Yu, W.⁷

27
- 0032556452
- Jin, M. Z.; Yang, L.; Wu, L. M.; Liu, Y. C.; Liu, Z. L. Chem. Commun. 1998, 2451.
- (1998) Chem. Commun , pp. 2451
- Jin, M.Z.¹ Yang, L.² Wu, L.M.³ Liu, Y.C.⁴ Liu, Z.L.⁵

28
- 0037164657
- Zhang, J.; Jin, M. Z.; Zhang, W.; Yang, L.; Liu, Z. L. Tetrahedron Lett. 2002, 43, 9687.
- (2002) Tetrahedron Lett , vol.43 , pp. 9687
- Zhang, J.¹ Jin, M.Z.² Zhang, W.³ Yang, L.⁴ Liu, Z.L.⁵

29
- 0026779021
- (a) Cabrera, A.; Alper, H. Tetrahedron Lett. 1992, 33, 5007.
- (1992) Tetrahedron Lett , vol.33 , pp. 5007
- Cabrera, A.¹ Alper, H.²

30
- 0026702716
- (b) Saburi, M.; Ohnuki, M.; Ogasawara, M.; Takahashi, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 5783.
- (1992) Tetrahedron Lett , vol.33 , pp. 5783
- Saburi, M.¹ Ohnuki, M.² Ogasawara, M.³ Takahashi, T.⁴ Uchida, Y.⁵

31
- 0032567945
- (c) Alonso, F.; Yus, M. Tetrahedron 1998, 54, 1921.
- (1998) Tetrahedron , vol.54 , pp. 1921
- Alonso, F.¹ Yus, M.²

32
- 0035967759
- (d) Sakaguchi, S.; Yamaga, T.; Ishii, Y. J. Org. Chem. 2001, 66, 4710.
- (2001) J. Org. Chem , vol.66 , pp. 4710
- Sakaguchi, S.¹ Yamaga, T.² Ishii, Y.³

33
- 0037474679
- (e) Lee, H. Y.; An, M. Tetrahedron Lett. 2003, 44, 2775.
- (2003) Tetrahedron Lett , vol.44 , pp. 2775
- Lee, H.Y.¹ An, M.²

34
- 14644435717
- and references cited therein
- Saikia, A.; Barthakur, M. G.; Boruah, R. C. Synlett 2005, 523 and references cited therein.
- (2005) Synlett , pp. 523
- Saikia, A.¹ Barthakur, M.G.² Boruah, R.C.³

35
- 0000360667
- Besides the catalysts noted by Ref. 3, see also: (a) Gase, R. A.; Pandit, U. K. J. Am. Chem. Soc. 1979, 101, 7059.
- Besides the catalysts noted by Ref. 3, see also: (a) Gase, R. A.; Pandit, U. K. J. Am. Chem. Soc. 1979, 101, 7059.

36
- 0023273768
- (b) Fujii, M.; Nakamura, K.; Yasui, S.; Ona, S.; Ohno, A. Bull. Chem. Soc. Jpn. 1987, 60, 2423.
- (1987) Bull. Chem. Soc. Jpn , vol.60 , pp. 2423
- Fujii, M.¹ Nakamura, K.² Yasui, S.³ Ona, S.⁴ Ohno, A.⁵

37
- 45249122389
- Typical experimental procedure: A mixture of 1 (2 mmol) and HEH (2.2 mmol) was refluxed under Ar in xylene (5 mL) for the time listed in Table 2. The solvent was evaporated and the residue was subjected to chromatography on a silica gel column with chloroform as eluent and identified by 1H or 13C NMR and HRMS. Representive spectrum data: compound 2d: 1H NMR (CDCl3, 300 MHz) δ: 7.94 (d, J=7.5 Hz, 2H, 7.42-7.56 (m, 3H, 7.16-7.27 (m, 4H, 3.28 (t, J=7.5 Hz, 2H, 3.04 (t, J=7.5 Hz, 2H, 13C NMR (CDCl3, 75 MHz) δ: 198.8, 139.8, 136.9, 133.2, 129.9, 128.7, 128.6, 128.1, 40.1, 29.4; HRMS calcd for C15H1335ClO 244.0655, found 244.0648; compound 2h: 1H NMR (CDCl3, 300 MHz) δ: 7.94 (d, J=8.7 Hz, 2H, 7.19-7.29 (m, 5H, 6.92 (d, J=9 Hz, 2H, 3.25 (t, J=7.8 Hz, 2H, 3.05 t, J=7.5 Hz, 2H
- 2 240.1150, found 240.1145.

38
- 0037149948
- Jiang, H.; Liu, Y. C.; Li, J.; Wang, G. W.; Wu, Y. D.; Wang, Q. M.; Mak, T. C. W. Chem. Commun. 2002, 882.
- (2002) Chem. Commun , pp. 882
- Jiang, H.¹ Liu, Y.C.² Li, J.³ Wang, G.W.⁴ Wu, Y.D.⁵ Wang, Q.M.⁶ Mak, T.C.W.⁷

39
- 0002621288
- (a) Zhu, X. Q.; Liu, Y. C.; Li, J.; Wang, H. Y. J. Chem. Soc., Perkin Trans. 2 1997, 2191.
- (1997) J. Chem. Soc., Perkin Trans. 2 , pp. 2191
- Zhu, X.Q.¹ Liu, Y.C.² Li, J.³ Wang, H.Y.⁴

40
- 0032761362
- (b) Zhu, X. Q.; Liu, Y. C.; Cheng, J. P. J. Org. Chem. 1999, 64, 8980.
- (1999) J. Org. Chem , vol.64 , pp. 8980
- Zhu, X.Q.¹ Liu, Y.C.² Cheng, J.P.³

41
- 0034286445
- (c) Zhu, X. Q.; Zou, H. L.; Yuan, P. W.; Liu, Y.; Cao, L.; Cheng, J. P. J. Chem. Soc., Perkin Trans. 2 2000, 1857.
- (2000) J. Chem. Soc., Perkin Trans. 2 , pp. 1857
- Zhu, X.Q.¹ Zou, H.L.² Yuan, P.W.³ Liu, Y.⁴ Cao, L.⁵ Cheng, J.P.⁶

42
- 0034553414
- (d) Zhu, X. Q.; Zhao, B. J.; Cheng, J. P. J. Org. Chem. 2000, 65, 8158.
- (2000) J. Org. Chem , vol.65 , pp. 8158
- Zhu, X.Q.¹ Zhao, B.J.² Cheng, J.P.³

43
- 1042268763
- (e) Dai, D. M.; Liu, Y. C.; Li, J. Chin. J. Chem. 2001, 19, 1217.
- (2001) Chin. J. Chem , vol.19 , pp. 1217
- Dai, D.M.¹ Liu, Y.C.² Li, J.³

44
- 0037078374
- (f) Wang, H. Y.; Dai, D. M.; Liu, Y. C.; Guo, Q. X. Tetrahedron Lett. 2002, 43, 7527.
- (2002) Tetrahedron Lett , vol.43 , pp. 7527
- Wang, H.Y.¹ Dai, D.M.² Liu, Y.C.³ Guo, Q.X.⁴

45
- 0037450133
- (g) Zhu, X. Q.; Li, H. R.; Li, Q.; Ai, T.; Lu, J. Y.; Yang, Y.; Cheng, J. P. Chem. Eur. J. 2003, 9, 871.
- (2003) Chem. Eur. J , vol.9 , pp. 871
- Zhu, X.Q.¹ Li, H.R.² Li, Q.³ Ai, T.⁴ Lu, J.Y.⁵ Yang, Y.⁶ Cheng, J.P.⁷

46
- 22544436666
- (h) Xu, H. J.; Dai, D. M.; Liu, Y. C.; Li, J.; Luo, S. W.; Wu, Y. D. Tetrahedron Lett. 2005, 46, 5739.
- (2005) Tetrahedron Lett , vol.46 , pp. 5739
- Xu, H.J.¹ Dai, D.M.² Liu, Y.C.³ Li, J.⁴ Luo, S.W.⁵ Wu, Y.D.⁶

47
- 33847215439
- (i) Xu, H. J.; Liu, Y. C.; Fu, Y. Chin. J. Chem. 2007, 25, 95.
- (2007) Chin. J. Chem , vol.25 , pp. 95
- Xu, H.J.¹ Liu, Y.C.² Fu, Y.³

48
- 2942637485
- Gȩbicki, J.; Marcinek, A.; Zielonka, J. Acc. Chem. Res. 2004, 37, 379.
- (2004) Acc. Chem. Res , vol.37 , pp. 379
- Gȩbicki, J.¹ Marcinek, A.² Zielonka, J.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.