SCOPUS 정보 검색 플랫폼

Volumn 7, Issue 17, 2009, Pages 3584-3593

The enantioselective benzoin condensation promoted by chiral triazolium precatalysts: Stereochemical control via hydrogen bonding

(2) O'Toole, Sarah E a Connon, Stephen J a

a TRINITY COLLEGE DUBLIN (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ALDEHYDE; BENZOIN CONDENSATION; CATALYST EVALUATION; CATALYTIC CYCLES; ENANTIOSELECTIVE; HYDROGEN BONDINGS; PRECATALYSTS; STEREOCHEMICAL CONTROL;

ALDEHYDES; CATALYSIS; CATALYSTS; CONDENSATION; HYDROGEN;

HYDROGEN BONDS;

EID: 70349286053 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b908517c Document Type: Article

Times cited : (57)

References (40)

1
- 84977252019
- F. Wöhler J. Liebig Ann. Pharm. 1832 3 249
- (1832) Ann. Pharm. , vol.3 , pp. 249
- Wöhler, F.¹ Liebig, J.²

2
- 84976755703
- N. Zinin Ann. Pharm. 1839 31 329
- (1839) Ann. Pharm. , vol.31 , pp. 329
- Zinin, N.¹

3
- 70349266616
- Recent reviews:
- N. Zinin Ann. Pharm. 1840 34 329
- (1840) Ann. Pharm. , vol.34 , pp. 329
- Zinin, N.¹

4
- 47049110202
- D. Enders O. Niemeier A. Henseler Chem. Rev. 2007 107 5506
- (2007) Chem. Rev. , vol.107 , pp. 5506
- Enders, D.¹ Niemeier, O.² Henseler, A.³

5
- 34250870731
- N. Marion S. Diez-Gonzalez S. P. Nolan Angew. Chem., Int. Ed. 2007 46 2988
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 2988
- Marion, N.¹ Diez-Gonzalez, S.² Nolan, S.P.³

6
- 28244479394
- K. Zeitler Angew. Chem., Int. Ed. 2005 44 7506
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 7506
- Zeitler, K.¹

7
- 18844424752
- M. Christmann Angew. Chem., Int. Ed. 2005 44 2632
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 2632
- Christmann, M.¹

8
- 4143051292
- D. Enders T. Balensiefer Acc. Chem. Res. 2004 37 534
- (2004) Acc. Chem. Res. , vol.37 , pp. 534
- Enders, D.¹ Balensiefer, T.²

9
- 2942611657
- J. S. Johnson Angew. Chem., Int. Ed. 2004 43 1326
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1326
- Johnson, J.S.¹

10
- 0000264556
- T. Ukai R. Tanaka T. Dokawa J. Pharm. Soc. Jpn. 1943 63 269
- (1943) J. Pharm. Soc. Jpn. , vol.63 , pp. 269
- Ukai, T.¹ Tanaka, R.² Dokawa, T.³

11
- 0001417463
- S. Mizuhara P. Handler J. Am. Chem. Soc. 1954 76 571
- (1954) J. Am. Chem. Soc. , vol.76 , pp. 571
- Mizuhara, S.¹ Handler, P.²

12
- 3142640259
- For a more recent kinetic study see:
- R. Breslow J. Am. Chem. Soc. 1958 80 3719
- (1958) J. Am. Chem. Soc. , vol.80 , pp. 3719
- Breslow, R.¹

13
- 0035958483
- M. J. White F. J. Leeper J. Org. Chem. 2001 66 5124
- (2001) J. Org. Chem. , vol.66 , pp. 5124
- White, M.J.¹ Leeper, F.J.²

14
- 0001715627
- J. Sheehan D. H. Hunnemann J. Am. Chem. Soc. 1966 88 3666
- (1966) J. Am. Chem. Soc. , vol.88 , pp. 3666
- Sheehan, J.¹ Hunnemann, D.H.²

15
- 0000757578
- Rawal later improved the yield of this process substantially to 48%:
- J. Sheehan T. Hara J. Org. Chem. 1974 39 1196
- (1974) J. Org. Chem. , vol.39 , pp. 1196
- Sheehan, J.¹ Hara, T.²

16
- 0032492979
- C. A. Dvorak V. H. Rawal Tetrahedron Lett. 1998 39 2925
- (1998) Tetrahedron Lett. , vol.39 , pp. 2925
- Dvorak, C.A.¹ Rawal, V.H.²

17
- 0000121695
- W. Takagi Y. Tamura Y. Yano Bull. Chem. Soc. Jpn. 1980 53 478
- (1980) Bull. Chem. Soc. Jpn. , vol.53 , pp. 478
- Takagi, W.¹ Tamura, Y.² Yano, Y.³

18
- 0027441447
- J. Marti J. Castells F. Lopez-Calahora Tetrahedron Lett. 1993 34 521
- (1993) Tetrahedron Lett. , vol.34 , pp. 521
- Marti, J.¹ Castells, J.² Lopez-Calahora, F.³

19
- 1642310428
- Y. Tachibana N. Kihara T. Takata J. Am. Chem. Soc. 2004 126 3438
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 3438
- Tachibana, Y.¹ Kihara, N.² Takata, T.³

20
- 0031007332
- R. L. Knight F. J. Leeper Tetrahedron Lett. 1997 38 3611
- (1997) Tetrahedron Lett. , vol.38 , pp. 3611
- Knight, R.L.¹ Leeper, F.J.²

21
- 0030920183
- A. U. Gerhard F. J. Leeper Tetrahedron Lett. 1997 38 3615
- (1997) Tetrahedron Lett. , vol.38 , pp. 3615
- Gerhard, A.U.¹ Leeper, F.J.²

22
- 33748608869
- R. L. Knight F. J. Leeper J. Chem. Soc., Perkin Trans. 1 1998 1891
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 1891
- Knight, R.L.¹ Leeper, F.J.²

23
- 4544371662
- J. Pesch K. Harms T. Bach Eur. J. Org. Chem. 2004 2025
- (2004) Eur. J. Org. Chem. , pp. 2025
- Pesch, J.¹ Harms, K.² Bach, T.³

24
- 0000430035
- D. Enders K. Breuer J. H. Teles Helv. Chim. Acta 1996 79 1217
- (1996) Helv. Chim. Acta , vol.79 , pp. 1217
- Enders, D.¹ Breuer, K.² Teles, J.H.³

25
- 0036263823
- D. Enders U. Kallfass Angew. Chem., Int. Ed. 2002 41 1743
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1743
- Enders, D.¹ Kallfass, U.²

26
- 47049097492
- D. Enders J. Han Tetrahedron: Asymmetry 2008 19 1367
- (2008) Tetrahedron: Asymmetry , vol.19 , pp. 1367
- Enders, D.¹ Han, J.²

27
- 33745716505
- D. Enders O. Niemeier T. Balensiefer Angew. Chem., Int. Ed. 2006 45 1463
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 1463
- Enders, D.¹ Niemeier, O.² Balensiefer, T.³

28
- 0037019628
- For a recent review see:
- M. S. Kerr J. Read de Alaniz T. Rovis J. Am. Chem. Soc. 2002 124 10298
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 10298
- Kerr, M.S.¹ Read De Alaniz, J.² Rovis, T.³

29
- 38949191992
- For related references concerning the enantioselective carbene-catalysed intramolecular benzoin condensation see:
- T. Rovis Chem. Lett. 2008 2
- (2008) Chem. Lett. , vol.2
- Rovis, T.¹

30
- 33745722719
- H. Takikawa Y. Hachisu J. W. Bode K. Suzuki Angew. Chem., Int. Ed. 2006 45 3492
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 3492
- Takikawa, H.¹ Hachisu, Y.² Bode, J.W.³ Suzuki, K.⁴

31
- 34547424960
- Very recently, You et al. reported a bis-triazolium precatalyst which was capable of promoting highly enantioselective benzoin condensation reactions:
- H. Takikawa K. Suzuki Org. Lett. 2007 9 2713
- (2007) Org. Lett. , vol.9 , pp. 2713
- Takikawa, H.¹ Suzuki, K.²

32
- 56649122062
- Houk and Dudding used computational methodologies to identify and examine the factors which influence enantioselectivity in these systems, see:
- Y. Ma S. Wei J. Wu F. Yang B. Liu J. Lan S. Yang J. You Adv. Synth. Catal. 2008 350 2645
- (2008) Adv. Synth. Catal. , vol.350 , pp. 2645
- Ma, Y.¹ Wei, S.² Wu, J.³ Yang, F.⁴ Liu, B.⁵ Lan, J.⁶ Yang, S.⁷ You, J.⁸

33
- 1942437578
- T. Dudding K. N. Houk Proc. Natl. Acad. Sci. U. S. A. 2004 101 5770
- (2004) Proc. Natl. Acad. Sci. U. S. A. , vol.101 , pp. 5770
- Dudding, T.¹ Houk, K.N.²

34
- 12744273171
- S. M. Mennen J. T. Blank M. B. Tran-Dubé J. E. Imbriglio S. J. Miller Chem. Commun. 2005 195
- (2005) Chem. Commun. , pp. 195
- Mennen, S.M.¹ Blank, J.T.² Tran-Dubé, M.B.³ Imbriglio, J.E.⁴ Miller, S.J.⁵

35
- 13644269271
- S. M. Mennen J. D. Gipson Y. R. Kim S. J. Miller J. Am. Chem. Soc. 2005 127 1654
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 1654
- Mennen, S.M.¹ Gipson, J.D.² Kim, Y.R.³ Miller, S.J.⁴

36
- 51949115828
- L. He Y. -R. Zhang X. -L. Huang S. Ye Synthesis 2008 2825
- (2008) Synthesis , pp. 2825
- He, L.¹ Z. Y, -R.² H. X, -L.³ Ye, S.⁴

37
- 56749102621
- H. Lv Y. -R. Zhang X. -L. Huang S. Ye Adv. Synth. Catal. 2008 350 2715
- (2008) Adv. Synth. Catal. , vol.350 , pp. 2715
- Lv, H.¹ Z. Y, -R.² H. X, -L.³ Ye, S.⁴

38
- 37049141021
- G. V. Boyd S. R. Dando J. Chem. Soc. (C) 1970 1397
- (1970) J. Chem. Soc. (C) , pp. 1397
- Boyd, G.V.¹ Dando, S.R.²

39
- 37049142015
- 1H NMR spectroscopy) for a significant conformational discrepancy between 15a and 16. In addition it is noteworthy that 15a and 16 display almost identical reactivity under these conditions and that all of the secondary amide catalysts evaluated promoted more selective reactions than 16. This we feel is best explained by the intermediacy of hydrogen-bonded species using precatalyst 15a
- G. V. Boyd A. J. H. Summers J. Chem. Soc. (C) 1971 409
- (1971) J. Chem. Soc. (C) , pp. 409
- Boyd, G.V.¹ Summers, A.J.H.²

40
- 37049112866
- A. J. Bellany L. Maclean J. Chem. Soc., Perkin Trans. 1 1979 204
- (1979) J. Chem. Soc., Perkin Trans. 1 , pp. 204
- Bellany, A.J.¹ MacLean, L.²

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