SCOPUS 정보 검색 플랫폼

Volumn 8, Issue 17, 2010, Pages 3918-3922

DOSY NMR for monitoring self aggregation of bifunctional organocatalysts: Increasing enantioselectivity with decreasing catalyst concentration

(7) Jang, Hyeong Bin a Rho, Ho Sik a,b Oh, Joong Suk a Nam, Eun Hye a Park, Sang Eun a Bae, Han Yong a Song, Choong Eui a

a Sungkyunkwan University (South Korea)

b AmorePacific Corporation (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BI-FUNCTIONAL CATALYSTS; BIFUNCTIONAL; CATALYST CONCENTRATION; CATALYST LOADINGS; DIFFUSION COEFFICIENTS; DOSY NMR; ORGANOCATALYSTS; SELF AGGREGATION; SELF-ASSOCIATIONS; SUBSTRATE CONCENTRATIONS;

ASSOCIATION REACTIONS; CONCENTRATION (PROCESS); ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; FUNCTIONAL GROUPS; SUBSTRATES;

CATALYSTS;

ARTICLE; CATALYSIS; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; DIFFUSION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

CATALYSIS; DIFFUSION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANIC CHEMISTRY PHENOMENA; STEREOISOMERISM;

EID: 77955481731 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c0ob00047g Document Type: Article

Times cited : (93)

References (37)

1
- 5344224096
- J.-A. Ma D. Cahard Angew. Chem. Int. Ed. 2004 43 4566 4583
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 4566-4583
- Ma, J.-A.¹ Cahard, D.²

2
- 4143104623
- C. Allemann R. Gordillo F. R. Clemente P. H.-Y. Cheong K. N. Houk Acc. Chem. Res. 2004 37 558 569
- (2004) Acc. Chem. Res. , vol.37 , pp. 558-569
- Allemann, C.¹ Gordillo, R.² Clemente, F.R.³ Cheong, P.H.-Y.⁴ Houk, K.N.⁵

3
- 0003458664
- K. Drauz, H. Waldmann Wiley-VCH, New York
- Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook (eds), K. Drauz, H. Waldmann, Wiley-VCH, New York, 1995
- (1995) Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook (Eds)

4
- 0004052643
- R. B. Silverman, Academic Press, New York
- The Organic Chemistry of Enzyme-Catalyzed Reactions ed., R. B. Silverman, Academic Press, New York, 2002
- (2002) The Organic Chemistry of Enzyme-Catalyzed Reactions Ed.

5
- 0000163641
- H. Hiemstra H. Wynberg J. Am. Chem. Soc. 1981 103 417 430
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 417-430
- Hiemstra, H.¹ Wynberg, H.²

6
- 47749122232
- A. Berkessel, H. Gröger, Wiley-VCH, Weinheim
- Asymmetric Organocatalysis (eds), A. Berkessel, H. Gröger, Wiley-VCH, Weinheim, 2005
- (2005) Asymmetric Organocatalysis (Eds)

7
- 43749108241
- P. I. Dalko, Wiley-VCH, Weinheim
- Enantioselective Organocatalysis (ed), P. I. Dalko, Wiley-VCH, Weinheim, 2007
- (2007) Enantioselective Organocatalysis (Ed)

8
- 38349142750
- (special issue on organocatalysis)
- B. List Chem. Rev. 2007 107 5413 5883
- (2007) Chem. Rev. , vol.107 , pp. 5413-5883
- List, B.¹

9
- 4143094833
- (special issue on asymmetric organocatalysis)
- K. N. Houk B. List Acc. Chem. Res. 2004 37 487 631
- (2004) Acc. Chem. Res. , vol.37 , pp. 487-631
- Houk, K.N.¹ List, B.²

10
- 33748766864
- B. List J. W. Yang Science 2006 313 1584 1586
- (2006) Science , vol.313 , pp. 1584-1586
- List, B.¹ Yang, J.W.²

11
- 52149113820
- For Reviews
- D. W. C. MacMillan Nature 2008 455 304 308
- (2008) Nature , vol.455 , pp. 304-308
- MacMillan, D.W.C.¹

12
- 29844448114
- Y. Takemoto Org. Biomol. Chem. 2005 3 4299 4306
- (2005) Org. Biomol. Chem. , vol.3 , pp. 4299-4306
- Takemoto, Y.¹

13
- 33646468489
- M. S. Taylor E. N. Jacobsen Angew. Chem. Int. Ed. 2006 45 1520 1543
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1520-1543
- Taylor, M.S.¹ Jacobsen, E.N.²

14
- 33845220042
- T. Marcelli J. H. van Maarseveen H. Hiemstra Angew. Chem. Int. Ed. 2006 45 7496 7504
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7496-7504
- Marcelli, T.¹ Van Maarseveen, J.H.² Hiemstra, H.³

15
- 33746277515
- S. J. Connon Chem. Eur. J. 2006 12 5418
- (2006) Chem. Eur. J. , vol.12 , pp. 5418
- Connon, S.J.¹

16
- 44349168328
- A mechanism study on bifunctional catalysis by tertiary amino-thiourea catalysts
- S. J. Connon Chem. Commun. 2008 2499 2510
- (2008) Chem. Commun. , pp. 2499-2510
- Connon, S.J.¹

17
- 37549041739
- S. J. Zuend E. N. Jacobsen J. Am. Chem. Soc. 2007 129 15872 15883
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 15872-15883
- Zuend, S.J.¹ Jacobsen, E.N.²

18
- 55549133297
- The quinine and hydroquinine squaramide, 4a and 4b, respectively, used in this study were prepared according to the procedure for cinchonine analogue reported in the above literature
- J. P. Malerich K. Hagihara V. H. Rawal J. Am. Chem. Soc. 2008 130 14416 14417
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14416-14417
- Malerich, J.P.¹ Hagihara, K.² Rawal, V.H.³

19
- 11844302258
- T. Okino Y. Hoashi T. Furukawa X. Xu Y. Takemoto J. Am. Chem. Soc. 2005 127 119 125
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 119-125
- Okino, T.¹ Hoashi, Y.² Furukawa, T.³ Xu, X.⁴ Takemoto, Y.⁵

20
- 17444385209
- A. Berkessel S. Mukherjee F. Cleeman Müller J. Lex Chem. Commun. 2005 1898 1900
- (2005) Chem. Commun. , pp. 1898-1900
- Berkessel, A.¹ Mukherjee, S.² Cleeman, F.³ Müller⁴ Lex, J.⁵

21
- 13444270903
- See the CIF-file in the Supporting Information of the Ref. 7
- A. Berkessel F. Cleeman S. Mukherjee T. N. Müller J. Lex Angew. Chem. Int. Ed. 2005 44 807 811
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 807-811
- Berkessel, A.¹ Cleeman, F.² Mukherjee, S.³ Müller, T.N.⁴ Lex, J.⁵

22
- 53849086148
- G. Tárkányi P. Király S. Varga B. Vakulya T. Soós Chem. Eur. J. 2008 14 6078 6086
- (2008) Chem. Eur. J. , vol.14 , pp. 6078-6086
- Tárkányi, G.¹ Király, P.² Varga, S.³ Vakulya, B.⁴ Soós, T.⁵

23
- 73949129298
- A recent mechanism study on bifunctional catalysis by natural cinchona alkaloids
- P. Király T. Soós S. Varga B. Vakulya G. Tárkányi Magn. Reson. Chem. 2010 48 13 19
- (2010) Magn. Reson. Chem. , vol.48 , pp. 13-19
- Király, P.¹ Soós, T.² Varga, S.³ Vakulya, B.⁴ Tárká nyi, G.⁵

24
- 68349123411
- C. S. Cucinotta M. Kosa P. Melchiorre A. Cavalli F. L. Gervasio Chem. Eur. J. 2009 15 7913 7921
- (2009) Chem. Eur. J. , vol.15 , pp. 7913-7921
- Cucinotta, C.S.¹ Kosa, M.² Melchiorre, P.³ Cavalli, A.⁴ Gervasio, F.L.⁵

25
- 40149101110
- H. S. Rho S. H. Oh J. W. Lee J. Y. Lee J. Chin C. E. Song Chem. Commun. 2008 1208 1210
- (2008) Chem. Commun. , pp. 1208-1210
- Rho, H.S.¹ Oh, S.H.² Lee, J.W.³ Lee, J.Y.⁴ Chin, J.⁵ Song, C.E.⁶

26
- 54749152753
- S. H. Oh H. S. Rho J. W. Lee J. E. Lee S. H. Youk J. Chin C. E. Song Angew. Chem. Int. Ed. 2008 47 7872 7875
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7872-7875
- Oh, S.H.¹ Rho, H.S.² Lee, J.W.³ Lee, J.E.⁴ Youk, S.H.⁵ Chin, J.⁶ Song, C.E.⁷

27
- 64549111802
- S. H. Youk S. H. Oh H. S. Rho J. E. Lee J. W. Lee C. E. Song Chem. Commun. 2009 2220 2222
- (2009) Chem. Commun. , pp. 2220-2222
- Youk, S.H.¹ Oh, S.H.² Rho, H.S.³ Lee, J.E.⁴ Lee, J.W.⁵ Song, C.E.⁶

28
- 41849087359
- A. Peschiulli Y. K. Gun'ko S. J. Connon J. Org. Chem. 2008 73 2454 2457
- (2008) J. Org. Chem. , vol.73 , pp. 2454-2457
- Peschiulli, A.¹ Gun'Ko, Y.K.² Connon, S.J.³

29
- 50149119251
- A. Peschiulli C. Quigley S. Tallon Y. K. Gun'ko S. J. Connon J. Org. Chem. 2008 73 6409 6412
- (2008) J. Org. Chem. , vol.73 , pp. 6409-6412
- Peschiulli, A.¹ Quigley, C.² Tallon, S.³ Gun'Ko, Y.K.⁴ Connon, S.J.⁵

30
- 15444366940
- Due to the poor solubility of squaramide catalysts in organic solvents, we were not able to conduct the reaction under more highly concentrated conditions Although the squaramide-based catalysts 4 are poorly soluble in all organic solvents, they dissolved into the clear solution during the DKR reaction
- B.-J. Li L. Jiang M. Liu Y.-C. Chen L.-S. Ding Y. Wu Synlett 2005 603 606
- (2005) Synlett , pp. 603-606
- Li, B.-J.¹ Jiang, L.² Liu, M.³ Chen, Y.-C.⁴ Ding, L.-S.⁵ Wu, Y.⁶

31
- 0347359145
- C. S. Johnson Jr. Prog. Nucl. Magn. Reson. Spectrosc. 1999 34 203 256
- (1999) Prog. Nucl. Magn. Reson. Spectrosc. , vol.34 , pp. 203-256
- Johnson, Jr.C.S.¹

32
- 77955493582
- (special issue on 'NMR and diffusion')
- G. Morris Magn. Reson. Chem. 2002 20 S2
- (2002) Magn. Reson. Chem. , vol.20 , pp. 2
- Morris, G.¹

33
- 13244253788
- Y. Cohen L. Avram L. Frish Angew. Chem. Int. Ed. 2005 44 520 554
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 520-554
- Cohen, Y.¹ Avram, L.² Frish, L.³

34
- 77649277121
- 3 (0.1%, v /v) as an internal standard, see Tables S9 and S10);
- J. W. Lee T. H. Ryu J. S. Oh H. Y. Bae H. B. Jang C. E. Song Chem. Commun. 2009 7224 7226
- (2009) Chem. Commun. , pp. 7224-7226
- Lee, J.W.¹ Ryu, T.H.² Oh, J.S.³ Bae, H.Y.⁴ Jang, H.B.⁵ Song, C.E.⁶

35
- 0035619669
- Due to the poor solubility of squaramide catalysts in organic solvents, we were not able to determine the diffusion coefficients in these ranges of concentrations
- E. J. Cabrita S. Berger Magn. Reson. Chem. 2001 39 S142 S148
- (2001) Magn. Reson. Chem. , vol.39
- Cabrita, E.J.¹ Berger, S.²

36
- 0001660358
- J. Liang J. C. Ruble G. C. Fu J. Org. Chem. 1998 63 3154 3155
- (1998) J. Org. Chem. , vol.63 , pp. 3154-3155
- Liang, J.¹ Ruble, J.C.² Fu, G.C.³

37
- 19544393388
- B. Vakulya S. Varga A. Csámpai T. Soós Org. Lett. 2005 7 1967 1969
- (2005) Org. Lett. , vol.7 , pp. 1967-1969
- Vakulya, B.¹ Varga, S.² Csámpai, A.³ Soós, T.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.