SCOPUS 정보 검색 플랫폼

Volumn 5, Issue 2, 2007, Pages 267-275

Enantioselective synthesis of β2-amino acids using rhodium-catalyzed hydrogenation

(7) Hoen, Rob a Tiemersma Wegman, Theodora a Procuranti, Barbara b Lefort, Laurent b De Vries, Johannes G a,b Minnaard, Adriaan J a Feringa, Ben L a

a UNIVERSITY OF GRONINGEN (Netherlands)

b DSM RESEARCH (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDROGENATION; MOLECULAR STRUCTURE; OPTIMIZATION; RHODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

CATALYST STRUCTURES; LIGAND SYSTEMS; MONODENTATE PHOSPHORAMIDITES; RHODIUM CATALYZED HYDROGENATION;

AMINO ACIDS;

ALCOHOL DERIVATIVE; AMINO ACID; HYDROGEN; LIGAND; PEPTIDE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; STEREOISOMERISM; SYNTHESIS; TEMPERATURE;

ALCOHOLS; AMINO ACIDS; CATALYSIS; CHEMISTRY, ORGANIC; HYDROGEN; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; PEPTIDES; RHODIUM; STEREOISOMERISM; TEMPERATURE;

EID: 33846104860 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b615131k Document Type: Article

Times cited : (61)

References (59)

1
- 0034616815
- C. Claver E. Fernandez A. Gillon K. Heslop D. J. Hyett A. Martorell A. G. Orpen P. G. Pringle Chem. Commun. 2000 961
- (2000) Chem. Commun. , pp. 961
- Claver, C.¹ Fernandez, E.² Gillon, A.³ Heslop, K.⁴ Hyett, D.J.⁵ Martorell, A.⁶ Orpen, A.G.⁷ Pringle, P.G.⁸

2
- 0034703724
- M. van den Berg A. J. Minnaard E. P. Schudde J. van Esch A. H. M. de Vries J. G. de Vries B. L. Feringa J. Am. Chem. Soc. 2000 122 11539
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 11539
- Van Den Berg, M.¹ Minnaard, A.J.² Schudde, E.P.³ Van Esch, J.⁴ De Vries, A.H.M.⁵ De Vries, J.G.⁶ Feringa, B.L.⁷

3
- 0034602040
- M. T. Reetz G. Mehler Angew. Chem., Int. Ed. 2000 39 3889
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3889
- Reetz, M.T.¹ Mehler, G.²

4
- 33846114453
- J. G. de Vries and C. J. Elsevier, Wiley-VCH, Weinheim, Germany, ch. 28
- M. van den Berg, B. L. Feringa and A. J. Minnaard, in Handbook of Homogeneous Hydrogenation, ed., J. G. de Vries, and, C. J. Elsevier, Wiley-VCH, Weinheim, Germany, 2006, ch. 28
- (2006) Handbook of Homogeneous Hydrogenation, Ed.
- Van Den Berg, M.¹ Feringa, B.L.² Minnaard In, A.J.³

5
- 0004232165
- D. J. Ager, CRC Press, Boca Raton, 2nd edn, pp. 269-286
- J. G. de Vries, in Handbook of Chiral Chemicals, ed., D. J. Ager, CRC Press, Boca Raton, 2nd edn, 2005, pp. 269-286
- (2005) Handbook of Chiral Chemicals, Ed.
- De Vries In, J.G.¹

6
- 31144476049
- H. Guo K. Ding L. Dai Chin. Sci. Bull. 2004 49 2003
- (2004) Chin. Sci. Bull. , vol.49 , pp. 2003
- Guo, H.¹ Ding, K.² Dai, L.³

7
- 3843098473
- T. Jerphagnon J.-L. Renaud C. Bruneau Tetrahedron: Asymmetry 2004 15 2101
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 2101
- Jerphagnon, T.¹ Renaud, J.-L.² Bruneau, C.³

8
- 0037450022
- M. T. Reetz T. Sell A. Meiswinkel G. Mehler Angew. Chem., Int. Ed. 2003 42 790
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 790
- Reetz, M.T.¹ Sell, T.² Meiswinkel, A.³ Mehler, G.⁴

9
- 0038065528
- M. T. Reetz G. Mehler Tetrahedron Lett. 2003 44 4593
- (2003) Tetrahedron Lett. , vol.44 , pp. 4593
- Reetz, M.T.¹ Mehler, G.²

10
- 13244295023
- M. T. Reetz Chim. Oggi 2003 21 5
- (2003) Chim. Oggi , vol.21 , pp. 5
- Reetz, M.T.¹

11
- 3843149637
- M. T. Reetz G. Mehler A. Meiswinkel Tetrahedron: Asymmetry 2004 15 2165
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 2165
- Reetz, M.T.¹ Mehler, G.² Meiswinkel, A.³

12
- 4544286909
- M. T. Reetz X. Li Tetrahedron 2004 60 9709
- (2004) Tetrahedron , vol.60 , pp. 9709
- Reetz, M.T.¹ Li, X.²

13
- 18844381406
- M. T. Reetz X. Li Angew. Chem., Int. Ed. 2005 44 2959
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 2959
- Reetz, M.T.¹ Li, X.²

14
- 33746190664
- M. T. Reetz Y. Fu A. Meiswinkel Angew. Chem., Int. Ed. 2006 45 1412
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 1412
- Reetz, M.T.¹ Fu, Y.² Meiswinkel, A.³

15
- 33646888838
- M. T. Reetz M. Surowie Heterocycles 2006 67 567
- (2006) Heterocycles , vol.67 , pp. 567
- Reetz, M.T.¹ Surowie, M.²

16
- 0041495679
- D. Peña A. J. Minnaard J. A. F. Boogers A. H. M. de Vries J. G. de Vries B. L. Feringa Org. Biomol. Chem. 2003 1 1087
- (2003) Org. Biomol. Chem. , vol.1 , pp. 1087
- Peña, D.¹ Minnaard, A.J.² Boogers, J.A.F.³ De Vries, A.H.M.⁴ De Vries, J.G.⁵ Feringa, B.L.⁶

17
- 22144464492
- For a highlight see:
- R. Hoen J. A. F. Boogers H. Bernsmann A. J. Minnaard A. Meetsma T. D. Tiemersma-Wegman A. H. M. de Vries J. G. de Vries B. L. Feringa Angew. Chem., Int. Ed. 2005 44 4209
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 4209
- Hoen, R.¹ Boogers, J.A.F.² Bernsmann, H.³ Minnaard, A.J.⁴ Meetsma, A.⁵ Tiemersma-Wegman, T.D.⁶ De Vries, A.H.M.⁷ De Vries, J.G.⁸ Feringa, B.L.⁹

18
- 25644453557
- For recent examples see:
- J. Hartwig Nature 2005 437 487
- (2005) Nature , vol.437 , pp. 487
- Hartwig, J.¹

19
- 32544451795
- R. Hoen S. Leleu P. N. M. Botman V. A. M. Appelman B. L. Feringa H. Hiemstra A. J. Minnaard J. H. van Maarseveen Org. Biomol. Chem. 2006 4 613
- (2006) Org. Biomol. Chem. , vol.4 , pp. 613
- Hoen, R.¹ Leleu, S.² Botman, P.N.M.³ Appelman, V.A.M.⁴ Feringa, B.L.⁵ Hiemstra, H.⁶ Minnaard, A.J.⁷ Van Maarseveen, J.H.⁸

20
- 11244305467
- C. Simons U. Hanefeld I. W. C. E. Arends A. J. Minnaard T. Maschmeyer R. A. Sheldon Chem. Commun. 2004 2830
- (2004) Chem. Commun. , pp. 2830
- Simons, C.¹ Hanefeld, U.² Arends, I.W.C.E.³ Minnaard, A.J.⁴ Maschmeyer, T.⁵ Sheldon, R.A.⁶

21
- 25444510405
- L. Panella B. L. Feringa J. G. de Vries A. J. Minnaard Org. Lett. 2005 7 4177
- (2005) Org. Lett. , vol.7 , pp. 4177
- Panella, L.¹ Feringa, B.L.² De Vries, J.G.³ Minnaard, A.J.⁴

22
- 33644659716
- L. Panella A. M. Aleixandre G. J. Kruidhof J. Robertus B. L. Feringa J. G. de Vries A. J. Minnaard J. Org. Chem. 2006 71 2026
- (2006) J. Org. Chem. , vol.71 , pp. 2026
- Panella, L.¹ Aleixandre, A.M.² Kruidhof, G.J.³ Robertus, J.⁴ Feringa, B.L.⁵ De Vries, J.G.⁶ Minnaard, A.J.⁷

23
- 27744455370
- P. E. Nielsen, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
- Pseudo-peptides in drug discovery, ed., P. E. Nielsen, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2004
- (2004) Pseudo-peptides in Drug Discovery, Ed.

24
- 3843140728
- D. Seebach T. Kimmerlin R. ebesta M. A. Campo A. K. Beck Tetrahedron 2004 60 7455
- (2004) Tetrahedron , vol.60 , pp. 7455
- Seebach, D.¹ Kimmerlin, T.² Ebesta, R.³ Campo, M.A.⁴ Beck, A.K.⁵

25
- 0035471135
- R. P. Cheng S. H. Gellman W. F. DeGrado J. Am. Chem. Soc. 2001 101 3219
- (2001) J. Am. Chem. Soc. , vol.101 , pp. 3219
- Cheng, R.P.¹ Gellman, S.H.² Degrado, W.F.³

26
- 84886427213
- E. Juaristi and V. Soloshonok, Wiley, Hoboken, 2nd edn
- Enantioselective synthesis of β-amino acids, ed., E. Juaristi, and, V. Soloshonok, Wiley, Hoboken, 2nd edn, 2005
- (2005) Enantioselective Synthesis of β-amino Acids, Ed.

27
- 0037201534
- For a detailed review see:
- M. Liu M. P. Sibi Tetrahedron 2002 58 7991
- (2002) Tetrahedron , vol.58 , pp. 7991
- Liu, M.¹ Sibi, M.P.²

28
- 4043089374
- G. Lelais D. Seebach Biopolymers 2004 76 206
- (2004) Biopolymers , vol.76 , pp. 206
- Lelais, G.¹ Seebach, D.²

29
- 0032811713
- D. Seebach A. R. Boog W. B. Schweizer Eur. J. Org. Chem. 1999 335
- (1999) Eur. J. Org. Chem. , pp. 335
- Seebach, D.¹ Boog, A.R.² Schweizer, W.B.³

30
- 0028124764
- M. Akssira M. Boumzebra H. Kasmi M. L. Roumestant P. Viallefont Amino Acids 1994 7 79
- (1994) Amino Acids , vol.7 , pp. 79
- Akssira, M.¹ Boumzebra, M.² Kasmi, H.³ Roumestant, M.L.⁴ Viallefont, P.⁵

31
- 6744246047
- A. A. D'Souza M. Motevalli A. J. Robinson P. B. Wyatt J. Chem. Soc., Perkin Trans. 1 1995 1
- (1995) J. Chem. Soc., Perkin Trans. 1 , pp. 1
- D'Souza, A.A.¹ Motevalli, M.² Robinson, A.J.³ Wyatt, P.B.⁴

32
- 84942821680
- J. J. Talley (Monsanto Company), Method of preparation chiral β-amino acids, Patent EP 0396526, 1990
- (1990) Method of Preparation Chiral β-amino Acids, Patent EP 0396526
- Talley, J.J.¹

33
- 0001799024
- K. Balenovic N. Bregnant Tetrahedron 1959 5 44
- (1959) Tetrahedron , vol.5 , pp. 44
- Balenovic, K.¹ Bregnant, N.²

34
- 0010640546
- K. Kakimoto M. D. Armstrong J. Biol. Chem. 1961 236 3283
- (1961) J. Biol. Chem. , vol.236 , pp. 3283
- Kakimoto, K.¹ Armstrong, M.D.²

35
- 84942836990
- E. Testa G. Cignarella G. Pifferi S. Füresz M. T. Timbal P. Schiatti G. Maffi Farmaco, Ed. Sci. 1964 11 895
- (1964) Farmaco, Ed. Sci. , vol.11 , pp. 895
- Testa, E.¹ Cignarella, G.² Pifferi, G.³ Füresz, S.⁴ Timbal, M.T.⁵ Schiatti, P.⁶ Maffi, G.⁷

36
- 0018753078
- H. Yuki Y. Okamoto Y. J. Kobayashi J. Polym. Sci., Polym. Chem. Ed. 1979 17 3867
- (1979) J. Polym. Sci., Polym. Chem. Ed. , vol.17 , pp. 3867
- Yuki, H.¹ Okamoto, Y.² Kobayashi, Y.J.³

37
- 0032884787
- S. Abele P. Seiler D. Seebach Helv. Chim. Acta 1999 82 1559
- (1999) Helv. Chim. Acta , vol.82 , pp. 1559
- Abele, S.¹ Seiler, P.² Seebach, D.³

38
- 33744826542
- Y. Chi S. H. Gellman J. Am. Chem. Soc. 2006 128 6804
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 6804
- Chi, Y.¹ Gellman, S.H.²

39
- 0002764426
- J. F. Bower J. M. J. Williams Synlett 1996 685
- (1996) Synlett , pp. 685
- Bower, J.F.¹ Williams, J.M.J.²

40
- 0010315056
- J. F. Bower R. Jumnah A. C. Williams J. M. J. Williams J. Chem. Soc., Perkin Trans. 1 1997 1411
- (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 1411
- Bower, J.F.¹ Jumnah, R.² Williams, A.C.³ Williams, J.M.J.⁴

41
- 0037124920
- H. M. L. Davies C. Venkataramani Angew. Chem., Int. Ed. 2002 41 2197
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2197
- Davies, H.M.L.¹ Venkataramani, C.²

42
- 0037414323
- A. Duursma A. J. Minnaard B. L. Feringa J. Am. Chem. Soc. 2003 125 3700
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 3700
- Duursma, A.¹ Minnaard, A.J.² Feringa, B.L.³

43
- 0037449670
- U. Eilitz F. Lessmann O. Seidelmann V. Wendisch Tetrahedron: Asymmetry 2003 14 189
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 189
- Eilitz, U.¹ Lessmann, F.² Seidelmann, O.³ Wendisch, V.⁴

44
- 1642352712
- U. Eilitz F. Lessmann O. Seidelmann V. Wendisch Tetrahedron: Asymmetry 2003 14 3095
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 3095
- Eilitz, U.¹ Lessmann, F.² Seidelmann, O.³ Wendisch, V.⁴

45
- 0038813824
- A. Rimkus N. Sewald Org. Lett. 2003 5 79
- (2003) Org. Lett. , vol.5 , pp. 79
- Rimkus, A.¹ Sewald, N.²

46
- 0035874739
- A. J. Robinson C. Y. Lim L. He P. Ma H.-Y. Li J. Org. Chem. 2001 66 4141
- (2001) J. Org. Chem. , vol.66 , pp. 4141
- Robinson, A.J.¹ Lim, C.Y.² He, L.³ Ma, P.⁴ Li, H.-Y.⁵

47
- 0035911373
- D. Saylik E. M. Campi A. C. Donohue W. R. Jackson A. J. Robinson Tetrahedron: Asymmetry 2001 12 657
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 657
- Saylik, D.¹ Campi, E.M.² Donohue, A.C.³ Jackson, W.R.⁴ Robinson, A.J.⁵

48
- 27644578586
- J. Elaridi A. Thaqi A. Prosser W. R. Jackson A. J. Robinson Tetrahedron: Asymmetry 2005 16 1309
- (2005) Tetrahedron: Asymmetry , vol.16 , pp. 1309
- Elaridi, J.¹ Thaqi, A.² Prosser, A.³ Jackson, W.R.⁴ Robinson, A.J.⁵

49
- 0037065328
- D. Peña A. J. Minnaard J. G. de Vries B. L. Feringa J. Am. Chem. Soc. 2002 124 14552
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 14552
- Peña, D.¹ Minnaard, A.J.² De Vries, J.G.³ Feringa, B.L.⁴

50
- 3042743885
- Y. Fu X.-X. Guo S.-F. Zhu A.-G. Hu J.-H. Xie Q.-L. Zhou J. Org. Chem. 2004 69 4648
- (2004) J. Org. Chem. , vol.69 , pp. 4648
- Fu, Y.¹ Guo, X.-X.² Zhu, S.-F.³ Hu, A.-G.⁴ Xie, J.-H.⁵ Zhou, Q.-L.⁶

51
- 33746925195
- H. Huang H. Liu J. Deng M. Qui Z. Zheng Org. Lett. 2006 8 3359
- (2006) Org. Lett. , vol.8 , pp. 3359
- Huang, H.¹ Liu, H.² Deng, J.³ Qui, M.⁴ Zheng, Z.⁵

52
- 0037366617
- D. Basavaiah A. J. Rao T. Satyanarayana Chem. Rev. 2003 103 811
- (2003) Chem. Rev. , vol.103 , pp. 811
- Basavaiah, D.¹ Rao, A.J.² Satyanarayana, T.³

53
- 1642286023
- D. Basavaiah T. Satyanarayana Chem. Commun. 2004 32
- (2004) Chem. Commun. , pp. 32
- Basavaiah, D.¹ Satyanarayana, T.²

54
- 13244251142
- Initial attempts to determine the ee by chiral GC or normal phase HPLC were not successful, since separations of substrate/product or enantiomers were not obtained
- H. Bernsmann M. van den Berg R. Hoen A. J. Minnaard G. Mehler M. T. Reetz J. G. de Vries B. L. Feringa J. Org. Chem. 2005 70 943
- (2005) J. Org. Chem. , vol.70 , pp. 943
- Bernsmann, H.¹ Van Den Berg, M.² Hoen, R.³ Minnaard, A.J.⁴ Mehler, G.⁵ Reetz, M.T.⁶ De Vries, J.G.⁷ Feringa, B.L.⁸

55
- 2942599460
- "Supplement to chiral technologies"
- L. Lefort J. A. F. Boogers A. H. M. de Vries J. G. de Vries Org. Lett. 2004 6 1733
- (2004) Org. Lett. , vol.6 , pp. 1733
- Lefort, L.¹ Boogers, J.A.F.² De Vries, A.H.M.³ De Vries, J.G.⁴

56
- 19444387312
- A. H. M. de Vries L. Lefort J. A. F. Boogers J. G. de Vries D. J. Ager Chim. Oggi 2005 23 18
- (2005) Chim. Oggi , vol.23 , pp. 18
- De Vries, A.H.M.¹ Lefort, L.² Boogers, J.A.F.³ De Vries, J.G.⁴ Ager, D.J.⁵

57
- 3042789542
- A. Duursma L. Lefort J. A. F. Boogers A. H. M. de Vries J. G. de Vries A. J. Minnaard B. L. Feringa Org. Biomol. Chem. 2004 2 1682
- (2004) Org. Biomol. Chem. , vol.2 , pp. 1682
- Duursma, A.¹ Lefort, L.² Boogers, J.A.F.³ De Vries, A.H.M.⁴ De Vries, J.G.⁵ Minnaard, A.J.⁶ Feringa, B.L.⁷

58
- 33745445414
- J. G. de Vries L. Lefort Chem.-Eur. J. 2006 12 4722
- (2006) Chem.-Eur. J. , vol.12 , pp. 4722
- De Vries, J.G.¹ Lefort, L.²

59
- 0037048455
- Reaction was performed on 50 mmol scale Reaction was performed on 41 mmol scale.
- F. Coelho W. P. Almeida D. Veronese C. R. Mateus E. C. S. Lopes R. C. Rossi G. P. C. Silveira C. H. Pavam Tetrahedron 2002 58 7437
- (2002) Tetrahedron , vol.58 , pp. 7437
- Coelho, F.¹ Almeida, W.P.² Veronese, D.³ Mateus, C.R.⁴ Lopes, E.C.S.⁵ Rossi, R.C.⁶ Silveira, G.P.C.⁷ Pavam, C.H.⁸

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.