SCOPUS 정보 검색 플랫폼

Organic and Biomolecular Chemistry

Volumn 4, Issue 11, 2006, Pages 2097-2099

Enantioselective construction of quaternary carbon centre catalysed by bifunctional organocatalyst

(8) Liu, Tian Yu a Long, Jun a Li, Bang Jing b Jiang, Lin a Li, Rui b Wu, Yong a Ding, Li Sheng b Chen, Ying Chun a

a SICHUAN UNIVERSITY (China)

b CHENGDU INSTITUTE OF BIOLOGY (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYSTS; HYDROGEN BONDS; ORGANIC COMPOUNDS; SUBSTITUTION REACTIONS; VINYL RESINS;

CATALYTIC REACTION; MICHAEL ADDITION; QUATERNARY STEREOCENTRE; VINYL SULFONES;

CARBON;

ACETIC ACID DERIVATIVE; AMINO ACID; CYANOACETIC ACID; DIAMINE; DIVINYL SULFONE; SULFONE; THIOUREA;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; HYDROGEN BOND; STEREOISOMERISM; SYNTHESIS;

ACETIC ACIDS; AMINO ACIDS; CATALYSIS; DIAMINES; HYDROGEN BONDING; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SULFONES; THIOUREA;

EID: 33744823336 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b605871j Document Type: Article

Times cited : (150)

References (60)

1
- 6044269452
- Special issue, see:
- P. I. Dalko L. Moisan Angew. Chem., Int. Ed. 2004 43 5138
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 5138
- Dalko, P.I.¹ Moisan, L.²

2
- 33646558310
- Acc. Chem. Res., 2004, 37(8)
- (2004) Acc. Chem. Res.

3
- 15244343428
- For examples of bifunctional organocatalysts, see:
- J. Seayad B. List Org. Biomol. Chem. 2005 3 719
- (2005) Org. Biomol. Chem. , vol.3 , pp. 719
- Seayad, J.¹ List, B.²

4
- 0033520752
- Y. Iwabuchi M. Nakatani N. Yokoyama S. Hatakeyama J. Am. Chem. Soc. 1999 121 10219
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 10219
- Iwabuchi, Y.¹ Nakatani, M.² Yokoyama, N.³ Hatakeyama, S.⁴

5
- 3042770799
- S. Saaby M. Bella K. A. Jørgensen J. Am. Chem. Soc. 2004 126 8120
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 8120
- Saaby, S.¹ Bella, M.² Jørgensen, K.A.³

6
- 4043154104
- H. Li Y. Wang L. Tang L. Deng J. Am. Chem. Soc. 2004 126 9906
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 9906
- Li, H.¹ Wang, Y.² Tang, L.³ Deng, L.⁴

7
- 15744396095
- For a review on bifunctional organometallic catalysts, see:
- K. Matsui S. Takizawa H. Sasai J. Am. Chem. Soc. 2005 127 3680
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 3680
- Matsui, K.¹ Takizawa, S.² Sasai, H.³

8
- 0036625219
- For pioneering work on thiourea (or urea) organocatalysts, see:
- M. Shibasaki N. Yoshikawa Chem. Rev. 2002 102 2187
- (2002) Chem. Rev. , vol.102 , pp. 2187
- Shibasaki, M.¹ Yoshikawa, N.²

9
- 0003554758
- M. S. Sigman E. N. Jacobsen J. Am. Chem. Soc. 1998 120 4901
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 4901
- Sigman, M.S.¹ Jacobsen, E.N.²

10
- 0037189898
- P. Vachal E. N. Jacobsen J. Am. Chem. Soc. 2002 124 10012
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 10012
- Vachal, P.¹ Jacobsen, E.N.²

11
- 0037032312
- A. G. Wenzel E. N. Jacobsen J. Am. Chem. Soc. 2002 124 12964
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 12964
- Wenzel, A.G.¹ Jacobsen, E.N.²

12
- 1842555199
- G. D. Joly E. N. Jacobsen J. Am. Chem. Soc. 2004 126 4102
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 4102
- Joly, G.D.¹ Jacobsen, E.N.²

13
- 4344713238
- M. S. Taylor E. N. Jacobsen J. Am. Chem. Soc. 2004 126 10558
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 10558
- Taylor, M.S.¹ Jacobsen, E.N.²

14
- 12344267138
- T. P. Yoon E. N. Jacobsen Angew. Chem., Int. Ed. 2005 44 466
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 466
- Yoon, T.P.¹ Jacobsen, E.N.²

15
- 21244472590
- D. E. Fuerst E. N. Jacobsen J. Am. Chem. Soc. 2005 127 8964
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 8964
- Fuerst, D.E.¹ Jacobsen, E.N.²

16
- 27444443731
- M. S. Taylor N. Tokunaga E. N. Jacobsen Angew. Chem., Int. Ed. 2005 44 6700
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6700
- Taylor, M.S.¹ Tokunaga, N.² Jacobsen, E.N.³

17
- 0142072631
- T. Okino Y. Hoashi Y. Takemoto J. Am. Chem. Soc. 2003 125 12672
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 12672
- Okino, T.¹ Hoashi, Y.² Takemoto, Y.³

18
- 11844302258
- T. Okino Y. Hoashi T. Furukawa X. Xu Y. Takemoto J. Am. Chem. Soc. 2005 127 119
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 119
- Okino, T.¹ Hoashi, Y.² Furukawa, T.³ Xu, X.⁴ Takemoto, Y.⁵

19
- 21244471124
- Y. Hoashi T. Okino Y. Takemoto Angew. Chem., Int. Ed. 2005 44 4032
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 4032
- Hoashi, Y.¹ Okino, T.² Takemoto, Y.³

20
- 15444366940
- B.-J. Li L. Jiang M. Liu Y.-C. Chen L.-S. Ding Y. Wu SYNLETT 2005 603
- (2005) SYNLETT , pp. 603
- Li, B.-J.¹ Jiang, L.² Liu, M.³ Chen, Y.-C.⁴ Ding, L.-S.⁵ Wu, Y.⁶

21
- 19544393388
- B. Vakulya S. Varga A. Csampai T. Sóos Org. Lett. 2005 7 1967
- (2005) Org. Lett. , vol.7 , pp. 1967
- Vakulya, B.¹ Varga, S.² Csampai, A.³ Sóos, T.⁴

22
- 13444270903
- A. Berkessel F. Cleemann S. Mukherjee T. N. Müller J. Lex Angew. Chem., Int. Ed. 2005 44 807
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 807
- Berkessel, A.¹ Cleemann, F.² Mukherjee, S.³ Müller, T.N.⁴ Lex, J.⁵

23
- 17444385209
- A. Berkessel S. Mukherjee F. Cleemann T. N. Müller J. Lex Chem. Commun. 2005 1898
- (2005) Chem. Commun. , pp. 1898
- Berkessel, A.¹ Mukherjee, S.² Cleemann, F.³ Müller, T.N.⁴ Lex, J.⁵

24
- 25444473664
- J. Ye D. J. Dixon P. S. Hynes Chem. Commun. 2005 4481
- (2005) Chem. Commun. , pp. 4481
- Ye, J.¹ Dixon, D.J.² Hynes, P.S.³

25
- 33644747543
- A. L. Tillman J. Ye D. J. Dixon Chem. Commun. 2006 1191
- (2006) Chem. Commun. , pp. 1191
- Tillman, A.L.¹ Ye, J.² Dixon, D.J.³

26
- 26844450640
- S. H. McCooey S. J. Connon Angew. Chem., Int. Ed. 2005 44 6367
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6367
- McCooey, S.H.¹ Connon, S.J.²

27
- 25444432564
- J. Wang H. Li X. Yu L. Zu W. Wang Org. Lett. 2005 7 4293
- (2005) Org. Lett. , vol.7 , pp. 4293
- Wang, J.¹ Li, H.² Yu, X.³ Zu, L.⁴ Wang, W.⁵

28
- 32044463560
- T. Marcelli R. N. S. van der Haas J. H. van Maarseveen H. Hiemstra Angew. Chem., Int. Ed. 2006 45 929
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 929
- Marcelli, T.¹ Van Der Haas, R.N.S.² Van Maarseveen, J.H.³ Hiemstra, H.⁴

29
- 24944473938
- T. Honjo S. Sano M. Shiro Y. Nagao Angew. Chem., Int. Ed. 2005 44 5838
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 5838
- Honjo, T.¹ Sano, S.² Shiro, M.³ Nagao, Y.⁴

30
- 27144518078
- R. P. Herrera V. Sgarzani L. Bernardi A. Ricci Angew. Chem., Int. Ed. 2005 44 6576
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6576
- Herrera, R.P.¹ Sgarzani, V.² Bernardi, L.³ Ricci, A.⁴

31
- 27544433063
- For reviews on hydrogen-bonding interaction of organocatalysts, see:
- Y. Sohtome Y. Hashimoto K. Nagasawa Adv. Synth. Catal. 2005 347 1643
- (2005) Adv. Synth. Catal. , vol.347 , pp. 1643
- Sohtome, Y.¹ Hashimoto, Y.² Nagasawa, K.³

32
- 0346865819
- P. R. Schreiner Chem. Soc. Rev. 2003 32 289
- (2003) Chem. Soc. Rev. , vol.32 , pp. 289
- Schreiner, P.R.¹

33
- 4544221552
- P. M. Pihko Angew. Chem., Int. Ed. 2004 43 2062
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 2062
- Pihko, P.M.¹

34
- 29844448114
- Y. Takemoto Org. Biomol. Chem. 2005 3 4299
- (2005) Org. Biomol. Chem. , vol.3 , pp. 4299
- Takemoto, Y.¹

35
- 33646468489
- For general reviews, see:
- M. S. Taylor E. N. Jacobsen Angew. Chem., Int. Ed. 2006 45 1520
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 1520
- Taylor, M.S.¹ Jacobsen, E.N.²

36
- 0001078144
- C. M. Rayner Contemp. Org. Synth. 1996 3 499
- (1996) Contemp. Org. Synth. , vol.3 , pp. 499
- Rayner, C.M.¹

37
- 0000068310
- C. Najera J. M. Sansano Recent Res. Dev. Org. Chem. 1998 2 637
- (1998) Recent Res. Dev. Org. Chem. , vol.2 , pp. 637
- Najera, C.¹ Sansano, J.M.²

38
- 0041757975
- J.-E. Bäckvall R. Chinchilla C. Najera M. Yus Chem. Rev. 1998 98 2291
- (1998) Chem. Rev. , vol.98 , pp. 2291
- Bäckvall, J.-E.¹ Chinchilla, R.² Najera, C.³ Yus, M.⁴

39
- 1842461758
- Wiley-VCH Verlag Gmbh & Co. KGaA, Weinhein, Germany, pp. 104-150 For examples by using chiral auxiliary strategy, see:
- R. Dumeunier and I. E. Marko, Modern Carbonyl Olefination, Wiley-VCH Verlag Gmbh & Co. KGaA, Weinhein, Germany, 2004, pp. 104-150
- (2004) Modern Carbonyl Olefination
- Dumeunier, R.¹ Marko, I.E.²

40
- 0025903870
- J. d'Angelo G. Revial Tetrahedron: Asymmetry 1991 2 199
- (1991) Tetrahedron: Asymmetry , vol.2 , pp. 199
- D'Angelo, J.¹ Revial, G.²

41
- 0343415171
- D. Enders S. F. Müller G. Raabe J. Runsink Eur. J. Org. Chem. 2000 879
- (2000) Eur. J. Org. Chem. , pp. 879
- Enders, D.¹ Müller, S.F.² Raabe, G.³ Runsink, J.⁴

42
- 0037925372
- A. K. Sanki C. G. Suresh U. D. Falgune T. Pathak Org. Lett. 2003 5 1285
- (2003) Org. Lett. , vol.5 , pp. 1285
- Sanki, A.K.¹ Suresh, C.G.² Falgune, U.D.³ Pathak, T.⁴

43
- 0042352240
- J. J. Reddick J. Cheng W. R. Roush Org. Lett. 2003 5 1967
- (2003) Org. Lett. , vol.5 , pp. 1967
- Reddick, J.J.¹ Cheng, J.² Roush, W.R.³

44
- 3242726215
- D. Desmaële S. Delarue-Cochin C. Cave J. d'Angelo G. Morgant Org. Lett. 2004 6 2421
- (2004) Org. Lett. , vol.6 , pp. 2421
- Desmaële, D.¹ Delarue-Cochin, S.² Cave, C.³ D'Angelo, J.⁴ Morgant, G.⁵

45
- 0034607673
- For recent studies on chiral auxiliary strategy, see:
- B. Ravindran K. Sakthivel C. G. Suresh T. Pathak J. Org. Chem. 2000 65 2637
- (2000) J. Org. Chem. , vol.65 , pp. 2637
- Ravindran, B.¹ Sakthivel, K.² Suresh, C.G.³ Pathak, T.⁴

46
- 33744808648
- and references therein For a Rh-catalysed enantioselective conjugate addition of organo-boronic acids to vinyl sulfones, see:
- J. Christoffers A. Mann Chem.-Eur. J. 2001 7 5
- (2001) Chem.-Eur. J. , vol.7 , pp. 5
- Christoffers, J.¹ Mann, A.²

47
- 4544306914
- P. Mauleón J. C. Carretero Org. Lett. 2004 6 3195
- (2004) Org. Lett. , vol.6 , pp. 3195
- Mauleón, P.¹ Carretero, J.C.²

48
- 27444447719
- P. Mauleón J. C. Carretero Chem. Commun. 2005 4961
- (2005) Chem. Commun. , pp. 4961
- Mauleón, P.¹ Carretero, J.C.²

49
- 21244480844
- H. Li J. Song X. Liu L. Deng J. Am. Chem. Soc. 2005 127 8948
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 8948
- Li, H.¹ Song, J.² Liu, X.³ Deng, L.⁴

50
- 26444568120
- For examples of intramolecular hydrogen bonding of sulfones in asymmetric synthesis, see:
- S. Mossé A. Alexakis Org. Lett. 2005 7 4361
- (2005) Org. Lett. , vol.7 , pp. 4361
- Mossé, S.¹ Alexakis, A.²

51
- 0033515733
- N. Mase Y. Watanabe T. Toru Tetrahedron Lett. 1999 40 2797
- (1999) Tetrahedron Lett. , vol.40 , pp. 2797
- Mase, N.¹ Watanabe, Y.² Toru, T.³

52
- 0034693340
- N. Mase Y. Watanabe T. Toru T. Kakumoto T. Hagiwara J. Org. Chem. 2000 65 7083
- (2000) J. Org. Chem. , vol.65 , pp. 7083
- Mase, N.¹ Watanabe, Y.² Toru, T.³ Kakumoto, T.⁴ Hagiwara, T.⁵

53
- 0032483733
- B. Gong C. Zheng E. Skrzypczak-Jankun Y. Yan J. Zhang J. Am. Chem. Soc. 1998 120 11194
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 11194
- Gong, B.¹ Zheng, C.² Skrzypczak-Jankun, E.³ Yan, Y.⁴ Zhang, J.⁵

54
- 0032727421
- Curran et al. has reported the hydrogen-bonding interaction of sulfoxide and biarylurea, see:
- B. Gong C. Zheng H. Zeng J. Zhu J. Am. Chem. Soc. 1999 121 9766
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 9766
- Gong, B.¹ Zheng, C.² Zeng, H.³ Zhu, J.⁴

55
- 33744821469
- For recent examples of enantioselective Michael addition of α-substituted cyanoacetates, see:
- D. P. Curran L. H. Kuo J. Org. Chem. 1994 59 3299
- (1994) J. Org. Chem. , vol.59 , pp. 3299
- Curran, D.P.¹ Kuo, L.H.²

56
- 0141725892
- M. S. Taylor E. N. Jacobsen J. Am. Chem. Soc. 2003 125 11204
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 11204
- Taylor, M.S.¹ Jacobsen, E.N.²

57
- 13644249902
- see ref. 8c For a recent review on catalytic enantioselective construction of all carbon quaternary chiral centres, see:
- M. S. Taylor D. N. Zalatan A. M. Lerchner E. N. Jacobsen J. Am. Chem. Soc. 2005 127 1313
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 1313
- Taylor, M.S.¹ Zalatan, D.N.² Lerchner, A.M.³ Jacobsen, E.N.⁴

58
- 27544458968
- and references therein For a highlight on enantiomerically pure β-amino acids, see:
- J. Christoffers A. Baro Adv. Synth. Catal. 2005 347 1473
- (2005) Adv. Synth. Catal. , vol.347 , pp. 1473
- Christoffers, J.¹ Baro, A.²

59
- 0347419949
- N. Sewald Angew. Chem., Int. Ed. 2003 42 5794
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5794
- Sewald, N.¹

60
- 0033986387
- It was found that the Michael addition of 2j to 5 could occur without any catalyst at room temperature Much poorer results were obtained in the presence of catalyst 1e (84% yield, 14% ee)
- S. Abele D. Seebach Eur. J. Org. Chem. 2000 1
- (2000) Eur. J. Org. Chem. , pp. 1
- Abele, S.¹ Seebach, D.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.