SCOPUS 정보 검색 플랫폼

Volumn 11, Issue 19, 2013, Pages 3223-3229

Diastereo- and enantioselective nitro-Mannich reaction of α-substituted nitroacetates to N-phosphoryl imines catalyzed by cinchona alkaloid thiourea organocatalysts

(5) Fan, Weidong a Kong, Shasha a Cai, Yan a Wu, Guiping a Miao, Zhiwei a

a NANKAI UNIVERSITY (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-SELECTIVITY; CHIRAL CENTERS; CINCHONA ALKALOID; DIASTEREO-SELECTIVITY; ENANTIOSELECTIVE; NITRO-MANNICH REACTION; ORGANOCATALYSTS; SYNTHETIC ROUTES;

ALKALOIDS; CATALYSTS; CHEMICAL REACTIONS; METABOLITES; THIOUREAS;

NITROGEN COMPOUNDS;

ACETIC ACID DERIVATIVE; CINCHONA ALKALOID; IMINE; NITROACETIC ACID; THIOUREA;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ACETATES; CATALYSIS; CINCHONA ALKALOIDS; CRYSTALLOGRAPHY, X-RAY; IMINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; THIOUREA;

CINCHONA;

EID: 84876949991 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c3ob40335a Document Type: Article

Times cited : (18)

References (51)

1
- 37549033533
- H. Zhou D. Peng B. Qin Z. R. Hou X. H. Liu X. M. Feng J. Org. Chem. 2007 72 10302
- (2007) J. Org. Chem. , vol.72 , pp. 10302
- Zhou, H.¹ Peng, D.² Qin, B.³ Hou, Z.R.⁴ Liu, X.H.⁵ Feng, X.M.⁶

2
- 58149204345
- C. Tan X. H. Liu L. W. Wang J. Wang X. M. Feng Org. Lett. 2008 10 5305
- (2008) Org. Lett. , vol.10 , pp. 5305
- Tan, C.¹ Liu, X.H.² Wang, L.W.³ Wang, J.⁴ Feng, X.M.⁵

3
- 0035902841
- N. Nishiwaki K. R. Knudsen K. V. Gothelf K. A. Jørgensen Angew. Chem., Int. Ed. 2001 40 2992
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2992
- Nishiwaki, N.¹ Knudsen, K.R.² Gothelf, K.V.³ Jørgensen, K.A.⁴

4
- 53849120983
- For reviews see
- B. Han Q. P. Liu R. Li X. Tian X. F. Xiong J. G. Deng Y. C. Chen Chem.-Eur. J. 2008 14 8094
- (2008) Chem.-Eur. J. , vol.14 , pp. 8094
- Han, B.¹ Liu, Q.P.² Li, R.³ Tian, X.⁴ Xiong, X.F.⁵ Deng, J.G.⁶ Chen, Y.C.⁷

5
- 24044496242
- A. Viso R. F. de la Pradilla A. García A. Flores Chem. Rev. 2005 105 3167
- (2005) Chem. Rev. , vol.105 , pp. 3167
- Viso, A.¹ De La Pradilla, R.F.² García, A.³ Flores, A.⁴

6
- 0346339657
- For selected examples see
- R. Ballini M. Petrini Tetrahedron 2004 60 1017
- (2004) Tetrahedron , vol.60 , pp. 1017
- Ballini, R.¹ Petrini, M.²

7
- 8644269566
- For reviews see
- L. Bernadi B. F. Bonini E. Capitò G. Dessole M. Comes-Franchini M. Fochi A. Ricci J. Org. Chem. 2004 69 8168
- (2004) J. Org. Chem. , vol.69 , pp. 8168
- Bernadi, L.¹ Bonini, B.F.² Capitò, E.³ Dessole, G.⁴ Comes-Franchini, M.⁵ Fochi, M.⁶ Ricci, A.⁷

8
- 0037434136
- B. Westermann Angew. Chem., Int. Ed. 2003 42 151
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 151
- Westermann, B.¹

9
- 37349005457
- A. Ting S. E. Schaus Eur. J. Org. Chem. 2007 5797
- (2007) Eur. J. Org. Chem. , pp. 5797
- Ting, A.¹ Schaus, S.E.²

10
- 66149117034
- E. Marqués-López P. Merino T. Tejero R. P. Herrera Eur. J. Org. Chem. 2009 2401
- (2009) Eur. J. Org. Chem. , pp. 2401
- Marqués-López, E.¹ Merino, P.² Tejero, T.³ Herrera, R.P.⁴

11
- 66449132403
- A. Puglisi L. Raimondi M. Benaglia M. Bonsignore S. Rossi Tetrahedron Lett. 2009 50 4340
- (2009) Tetrahedron Lett. , vol.50 , pp. 4340
- Puglisi, A.¹ Raimondi, L.² Benaglia, M.³ Bonsignore, M.⁴ Rossi, S.⁵

12
- 0033521210
- K. Yamada S. J. Harwood H. Gröger M. Shibasaki Angew. Chem., Int. Ed. 1999 38 3504
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 3504
- Yamada, K.¹ Harwood, S.J.² Gröger, H.³ Shibasaki, M.⁴

13
- 0034974140
- K. Yamada G. Moll M. Shibasaki Synlett 2001 980
- (2001) Synlett , pp. 980
- Yamada, K.¹ Moll, G.² Shibasaki, M.³

14
- 0034807178
- K. R. Knudsen T. Risgaard N. Nishiwaki K. V. Gothelf K. A. Jørgensen J. Am. Chem. Soc. 2001 123 5843
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 5843
- Knudsen, K.R.¹ Risgaard, T.² Nishiwaki, N.³ Gothelf, K.V.⁴ Jørgensen, K.A.⁵

15
- 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

16
- 1342268984
- T. Okino S. Nakamura T. Furukawa Y. Takemoto Org. Lett. 2004 6 625
- (2004) Org. Lett. , vol.6 , pp. 625
- Okino, T.¹ Nakamura, S.² Furukawa, T.³ Takemoto, Y.⁴

17
- 1642369984
- B. M. Nugent R. A. Yoder J. N. Johnston J. Am. Chem. Soc. 2004 126 3418
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 3418
- Nugent, B.M.¹ Yoder, R.A.² Johnston, J.N.³

18
- 33947648877
- Selected examples
- A. Singh R. A. Yoder B. Shen J. N. Johnston J. Am. Chem. Soc. 2007 129 3466
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 3466
- Singh, A.¹ Yoder, R.A.² Shen, B.³ Johnston, J.N.⁴

19
- 18444398945
- K. R. Knudsen K. A. Jørgensen Org. Biomol. Chem. 2005 3 1362
- (2005) Org. Biomol. Chem. , vol.3 , pp. 1362
- Knudsen, K.R.¹ Jørgensen, K.A.²

20
- 39549091935
- Z. Chen H. Morimoto S. Matsunaga M. Shibasaki J. Am. Chem. Soc. 2008 130 2170
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 2170
- Chen, Z.¹ Morimoto, H.² Matsunaga, S.³ Shibasaki, M.⁴

21
- 50249092090
- D. Uraguchi K. Koshimoto T. Ooi J. Am. Chem. Soc. 2008 130 10878
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 10878
- Uraguchi, D.¹ Koshimoto, K.² Ooi, T.³

22
- 42949158232
- A. Singh J. N. Johnston J. Am. Chem. Soc. 2008 130 5866
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 5866
- Singh, A.¹ Johnston, J.N.²

23
- 80054963906
- X. M. Hu C. M. Gao C. Y. Tan C. L. Zhang H. L. Zhang S. F. Li H. X. Liu Y. Y. Jiang Protein Pept. Lett. 2011 18 1258
- (2011) Protein Pept. Lett. , vol.18 , pp. 1258
- Hu, X.M.¹ Gao, C.M.² Tan, C.Y.³ Zhang, C.L.⁴ Zhang, H.L.⁵ Li, S.F.⁶ Liu, H.X.⁷ Jiang, Y.Y.⁸

24
- 84866423253
- N. F. Zakirova A. V. Shipitsyn M. V. Jasko M. M. Prokofjeva V. L. Andronova G. A. Galegov V. S. Prassolov S. N. Kochetkov Bioorg. Med. Chem. 2012 20 5802
- (2012) Bioorg. Med. Chem. , vol.20 , pp. 5802
- Zakirova, N.F.¹ Shipitsyn, A.V.² Jasko, M.V.³ Prokofjeva, M.M.⁴ Andronova, V.L.⁵ Galegov, G.A.⁶ Prassolov, V.S.⁷ Kochetkov, S.N.⁸

25
- 24044496242
- A. Viso R. Fernández de la Pradilla A. García A. Flores Chem. Rev. 2005 105 3167
- (2005) Chem. Rev. , vol.105 , pp. 3167
- Viso, A.¹ Fernández De La Pradilla, R.² García, A.³ Flores, A.⁴

26
- 4043061359
- U. J. Meierhenrich G. M. Muňoz Caro J. H. Bredehöft E. K. Jessberger W. H.-P. Thiemann Proc. Natl. Acad. Sci. U. S. A. 2004 101 9182
- (2004) Proc. Natl. Acad. Sci. U. S. A. , vol.101 , pp. 9182
- Meierhenrich, U.J.¹ Muňoz Caro, G.M.² Bredehöft, J.H.³ Jessberger, E.K.⁴ Thiemann, W.H.-P.⁵

27
- 34250877412
- J. H. Bredehöft K. Breme U. J. Meierhenrich S. V. Hoffmann W. H.-P. Thiemann Chirality 2007 19 570
- (2007) Chirality , vol.19 , pp. 570
- Bredehöft, J.H.¹ Breme, K.² Meierhenrich, U.J.³ Hoffmann, S.V.⁴ Thiemann, W.H.-P.⁵

28
- 0031044977
- A. Rosowsky C. M. Vaidya H. Bader J. E. Wright B. A. Teicher J. Med. Chem. 1997 40 286
- (1997) J. Med. Chem. , vol.40 , pp. 286
- Rosowsky, A.¹ Vaidya, C.M.² Bader, H.³ Wright, J.E.⁴ Teicher, B.A.⁵

29
- 0021914024
- W. J. Greenlee P. L. Allibone D. S. Perlow A. A. Patchett E. H. Ulm T. C. Vassil J. Med. Chem. 1985 28 434
- (1985) J. Med. Chem. , vol.28 , pp. 434
- Greenlee, W.J.¹ Allibone, P.L.² Perlow, D.S.³ Patchett, A.A.⁴ Ulm, E.H.⁵ Vassil, T.C.⁶

30
- 71349084983
- Selected examples
- D. Albuquerque J. Nihei F. Cardillo R. Singh Cell. Immunol. 2010 260 92
- (2010) Cell. Immunol. , vol.260 , pp. 92
- Albuquerque, D.¹ Nihei, J.² Cardillo, F.³ Singh, R.⁴

31
- 84865447147
- K. N. Gavrilov A. A. Shiryaev I. V. Chuchelkin S. V. Zheglov E. A. Rastorguev V. A. Davankov A. Börner Tetrahedron: Asymmetry 2012 23 1052
- (2012) Tetrahedron: Asymmetry , vol.23 , pp. 1052
- Gavrilov, K.N.¹ Shiryaev, A.A.² Chuchelkin, I.V.³ Zheglov, S.V.⁴ Rastorguev, E.A.⁵ Davankov, V.A.⁶ Börner, A.⁷

32
- 80054761033
- Y. Y. Han Z. J. Wu W. B. Chen X. L. Du X. M. Zhang W. C. Yuan Org. Lett. 2011 13 5064
- (2011) Org. Lett. , vol.13 , pp. 5064
- Han, Y.Y.¹ Wu, Z.J.² Chen, W.B.³ Du, X.L.⁴ Zhang, X.M.⁵ Yuan, W.C.⁶

33
- 80053199083
- K. Wilckens M. A. Duhs D. Lentz C. Czekelius X. L. Du X. M. Zhang W. C. Yuan Eur. J. Org. Chem. 2011 5441
- (2011) Eur. J. Org. Chem. , pp. 5441
- Wilckens, K.¹ Duhs, M.A.² Lentz, D.³ Czekelius, C.⁴ Du, X.L.⁵ Zhang, X.M.⁶ Yuan, W.C.⁷

34
- 62749104392
- N. A. Cortez G. Aguirre M. Parra-Hake R. Somanathan Tetrahedron Lett. 2009 50 2228
- (2009) Tetrahedron Lett. , vol.50 , pp. 2228
- Cortez, N.A.¹ Aguirre, G.² Parra-Hake, M.³ Somanathan, R.⁴

35
- 84865439001
- S. S. Kong W. D. Fan G. P. Wu Z. W. Miao Angew. Chem., Int. Ed. 2012 51 8864
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 8864
- Kong, S.S.¹ Fan, W.D.² Wu, G.P.³ Miao, Z.W.⁴

36
- 80052856345
- Z. J. Fang H. H. Yang Z. W. Miao R. Y. Chen Helv. Chim. Acta 2011 94 1586
- (2011) Helv. Chim. Acta , vol.94 , pp. 1586
- Fang, Z.J.¹ Yang, H.H.² Miao, Z.W.³ Chen, R.Y.⁴

37
- 70349300144
- Y. D. Wang Y. Y. Wang J. P. Yu Z. W. Miao R. Y. Chen Chem.-Eur. J. 2009 15 9290
- (2009) Chem.-Eur. J. , vol.15 , pp. 9290
- Wang, Y.D.¹ Wang, Y.Y.² Yu, J.P.³ Miao, Z.W.⁴ Chen, R.Y.⁵

38
- 55049093296
- For recent reviews on thiourea catalysis, see
- Y. D. Wang F. Wang Y. Y. Wang Z. W. Miao R. Y. Chen Adv. Synth. Catal. 2008 350 2339
- (2008) Adv. Synth. Catal. , vol.350 , pp. 2339
- Wang, Y.D.¹ Wang, F.² Wang, Y.Y.³ Miao, Z.W.⁴ Chen, R.Y.⁵

39
- 29844448114
- Y. Takemoto Org. Biomol. Chem. 2005 3 4299
- (2005) Org. Biomol. Chem. , vol.3 , pp. 4299
- Takemoto, Y.¹

40
- 33646468489
- 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

41
- 33746277515
- S. J. Connon Chem.-Eur. J. 2006 12 5418
- (2006) Chem.-Eur. J. , vol.12 , pp. 5418
- Connon, S.J.¹

42
- 38349135345
- A. G. Doyle E. N. Jacobsen Chem. Rev. 2007 107 5713
- (2007) Chem. Rev. , vol.107 , pp. 5713
- Doyle, A.G.¹ Jacobsen, E.N.²

43
- 44349168328
- S. J. Connon Chem. Commun. 2008 2499
- (2008) Chem. Commun. , pp. 2499
- Connon, S.J.¹

44
- 77951758941
- Y. Takemoto Chem. Pharm. Bull. 2010 58 593
- (2010) Chem. Pharm. Bull. , vol.58 , pp. 593
- Takemoto, Y.¹

45
- 73349112857
- For synthesis of the catalysts see
- Y. Y. Wang H. T. Yang J. P. Yu Z. W. Miao R. Y. Chen Adv. Synth. Catal. 2009 351 3057
- (2009) Adv. Synth. Catal. , vol.351 , pp. 3057
- Wang, Y.Y.¹ Yang, H.T.² Yu, J.P.³ Miao, Z.W.⁴ Chen, R.Y.⁵

46
- 34248196643
- L. Jiang H. T. Zheng T. Y. Liu L. Yue Y. C. Chen Tetrahedron 2007 63 5123
- (2007) Tetrahedron , vol.63 , pp. 5123
- Jiang, L.¹ Zheng, H.T.² Liu, T.Y.³ Yue, L.⁴ Chen, Y.C.⁵

47
- 19544393388
- B. Vakulya S. Varga A. Csámpai T. Soós Org. Lett. 2005 7 1967
- (2005) Org. Lett. , vol.7 , pp. 1967
- Vakulya, B.¹ Varga, S.² Csámpai, A.³ Soós, T.⁴

48
- 33947169944
- The preparation of the aromatic N-phosphoryl imines 4 see
- K. Liu H. F. Cui J. Nie K. Y. Dong X. J. Li J. A. Ma Org. Lett. 2007 9 923
- (2007) Org. Lett. , vol.9 , pp. 923
- Liu, K.¹ Cui, H.F.² Nie, J.³ Dong, K.Y.⁴ Li, X.J.⁵ Ma, J.A.⁶

49
- 0029895329
- A. Zwierzak A. Napieraj Tetrahedron 1996 52 8789
- (1996) Tetrahedron , vol.52 , pp. 8789
- Zwierzak, A.¹ Napieraj, A.²

50
- 79960957480
- Attempts to prepare the corresponding imines starting from aliphatic aldehydes, such as acrolein, failed due to the addition of diethyl phosphoroamidate to strongly electrophilic N-(diethylphosphoryl)prop-2-ene imine Crystallographic data for the structural analysis of compound 6a have been deposited at the Cambridge Crystallographic Data Centre as CCDC
- X. Y. Hao Q. Chen K. Yamada Y. Yamamoto K. Tomioka Tetrahedron 2011 67 6469
- (2011) Tetrahedron , vol.67 , pp. 6469
- Hao, X.Y.¹ Chen, Q.² Yamada, K.³ Yamamoto, Y.⁴ Tomioka, K.⁵

51
- 0003670186
- Wiley-VCH, Hoboken, New Jersey
- L. D. Quin and J. G. Verkade, Phosphorus-31 NMR spectral properties in compound characterization and structural analysis, Wiley-VCH, Hoboken, New Jersey, 1994
- (1994) Phosphorus-31 NMR Spectral Properties in Compound Characterization and Structural Analysis
- Quin, L.D.¹ Verkade, J.G.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.