SCOPUS 정보 검색 플랫폼

Volumn 7, Issue 3, 2009, Pages 518-526

Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones

(4) Alonso, Francisco a,b Davies, Stephen G a Elend, Almut S a Smith, Andrew D a

a UNIVERSITY OF OXFORD (United Kingdom)

b UNIVERSITY OF ALICANTE (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AMINES; ORGANIC ACIDS; THERMODYNAMICS;

AMINOBUTYRIC ACIDS; CYCLISATION; FERROCENECARBOXALDEHYDE; FERROCENYL; KINETIC CONTROLS; OXAZOLIDINONE; PHENYLGLYCINE; STEREOSELECTIVE FORMATIONS; TEMPERATURE DEPENDENCES; THERMODYNAMIC CONTROLS;

AMINO ACIDS;

ALANINE; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ENZYME SPECIFICITY; KINETICS; STEREOISOMERISM; TEMPERATURE; THERMODYNAMICS;

ALANINE; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXAZOLIDINONES; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TEMPERATURE; THERMODYNAMICS;

EID: 58849166835 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b814450h Document Type: Article

Times cited : (11)

References (29)

1
- 0003828324
- G. C. Barret, Chapman & Hall, London, pp. 227-245
- A. J. Jung, Chemistry and Biochemistry of the Amino Acids, ed., G. C. Barret, Chapman & Hall, London, 1985, pp. 227-245
- (1985) Chemistry and Biochemistry of the Amino Acids, Ed.
- Jung, A.J.¹

2
- 0023873774
- D. Schirlin F. Gerhart J. M. Horsperger M. Hamon J. Wagner M. J. Jung J. Med. Chem. 1988 31 30
- (1988) J. Med. Chem. , vol.31 , pp. 30
- Schirlin, D.¹ Gerhart, F.² Horsperger, J.M.³ Hamon, M.⁴ Wagner, J.⁵ Jung, M.J.⁶

3
- 0027478963
- D. E. Zembower J. A. Gilbert M. M. Ames J. Med. Chem. 1993 36 305
- (1993) J. Med. Chem. , vol.36 , pp. 305
- Zembower, D.E.¹ Gilbert, J.A.² Ames, M.M.³

4
- 0003416748
- J. E. Baldwin, P. D. Magnus, Pergamon Press, Oxford
- R. M. Williams, Synthesis of Optically Active α-Amino Acids, eds., J. E. Baldwin, P. D. Magnus, Pergamon Press, Oxford, 1989
- (1989) Synthesis of Optically Active α-Amino Acids, Eds.
- Williams, R.M.¹

5
- 0032561221
- C. Cativiela M. D. Díaz-de-Villegas Tetrahedron: Asymmetry 1998 9 3517
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3517
- Cativiela, C.¹ Díaz-De-Villegas, M.D.²

6
- 0034712270
- For a review, see:
- C. Cativiela M. D. Díaz-de-Villegas Tetrahedron: Asymmetry 2000 11 645
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 645
- Cativiela, C.¹ Díaz-De-Villegas, M.D.²

7
- 0030513164
- For examples see:
- D. Seebach A. R. Sting M. Hoffmann Angew. Chem., Int. Ed. Engl. 1996 35 2708
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2708
- Seebach, D.¹ Sting, A.R.² Hoffmann, M.³

8
- 33750800345
- D. Seebach B. Lamatsch R. Mastutz A. K. Beck M. Dobler M. Egli R. Fitzi M. Gautschi B. Herradon P. C. Hibder J. I. Irwin R. Locher M. Maestro T. Maetzke A. Mourino E. Pfammatter D. A. Plattner C. Schickli W. Bernd Schweizer P. Seiler G. Stucky Helv. Chim. Acta 1992 75 913
- (1992) Helv. Chim. Acta , vol.75 , pp. 913
- Seebach, D.¹ Lamatsch, B.² Mastutz, R.³ Beck, A.K.⁴ Dobler, M.⁵ Egli, M.⁶ Fitzi, R.⁷ Gautschi, M.⁸ Herradon, B.⁹ Hibder, P.C.¹⁰ Irwin, J.I.¹¹ Locher, R.¹² Maestro, M.¹³ Maetzke, T.¹⁴ Mourino, A.¹⁵ Pfammatter, E.¹⁶ Plattner, D.A.¹⁷ Schickli, C.¹⁸ Bernd Schweizer, W.¹⁹ Seiler, P.²⁰ Stucky, G.²¹ more..

9
- 0023864858
- M. Gander-Cooper D. Seebach Helv. Chim. Acta 1988 71 224
- (1988) Helv. Chim. Acta , vol.71 , pp. 224
- Gander-Cooper, M.¹ Seebach, D.²

10
- 84949114875
- E. Altmann K. Nebel M. Mutter Helv. Chim. Acta 1991 74 800
- (1991) Helv. Chim. Acta , vol.74 , pp. 800
- Altmann, E.¹ Nebel, K.² Mutter, M.³

11
- 0023772286
- K. Nebel M. Mutter Tetrahedron 1988 44 4793
- (1988) Tetrahedron , vol.44 , pp. 4793
- Nebel, K.¹ Mutter, M.²

12
- 84987505887
- For a complementary strategy that allows access to both cis- and trans-oxazolidinones stereoselectively from N-Cbz-(S)-Phe, see:
- D. Seebach E. Juaristi D. D. Miller C. Schickli T. Weber Helv. Chim. Acta 1987 70 237
- (1987) Helv. Chim. Acta , vol.70 , pp. 237
- Seebach, D.¹ Juaristi, E.² Miller, D.D.³ Schickli, C.⁴ Weber, T.⁵

13
- 0001713977
- Also see:
- M. J. O'Donnell Z. Fang X. Ma J. C. Huffman Heterocycles 1997 46 617.
- (1997) Heterocycles , vol.46 , pp. 617
- O'Donnell, M.J.¹ Fang, Z.² Ma, X.³ Huffman, J.C.⁴

14
- 0028799848
- W. D. Shrader C. K. Marlowe Bioorg. Med. Chem. Lett. 1995 5 2207
- (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 2207
- Shrader, W.D.¹ Marlowe, C.K.²

15
- 84956106373
- D. Seebach A. Fadel Helv. Chim. Acta 1985 68 1243
- (1985) Helv. Chim. Acta , vol.68 , pp. 1243
- Seebach, D.¹ Fadel, A.²

16
- 0000754192
- A. Fadel J. Salaün Tetrahedron Lett. 1987 28 2243
- (1987) Tetrahedron Lett. , vol.28 , pp. 2243
- Fadel, A.¹ Salaün, J.²

17
- 84986348006
- R. Naef D. Seebach Helv. Chim. Acta 1985 68 135
- (1985) Helv. Chim. Acta , vol.68 , pp. 135
- Naef, R.¹ Seebach, D.²

18
- 0035971998
- E. Napolitano V. Farina Tetrahedron Lett. 2001 42 3231
- (2001) Tetrahedron Lett. , vol.42 , pp. 3231
- Napolitano, E.¹ Farina, V.²

19
- 33749854297
- M. Eriksson E. Napolitano J. Xu S. Kapadia D. Byrne L. Nummy N. Grinberg S. Shen H. Lee V. Farina Chimia 2006 60 566
- (2006) Chimia , vol.60 , pp. 566
- Eriksson, M.¹ Napolitano, E.² Xu, J.³ Kapadia, S.⁴ Byrne, D.⁵ Nummy, L.⁶ Grinberg, N.⁷ Shen, S.⁸ Lee, H.⁹ Farina, V.¹⁰

20
- 0028898652
- F. Alonso S. G. Davies Tetrahedron: Asymmetry 1995 6 353
- (1995) Tetrahedron: Asymmetry , vol.6 , pp. 353
- Alonso, F.¹ Davies, S.G.²

21
- 33748623646
- F. Alonso S. G. Davies A. S. Elend J. L. Haggitt J. Chem. Soc., Perkin Trans. 1 1998 257
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 257
- Alonso, F.¹ Davies, S.G.² Elend, A.S.³ Haggitt, J.L.⁴

22
- 0005337494
- F. Alonso S. G. Davies C. A. P. Smethurst J. Organomet. Chem. 1998 553 463
- (1998) J. Organomet. Chem. , vol.553 , pp. 463
- Alonso, F.¹ Davies, S.G.² Smethurst, C.A.P.³

23
- 0003598098
- R. Scheffold, Springer Verlag, Berlin, pp. 174-176. For related examples see:
- D. Seebach, R. Imwinkelried, T. Weber, ed., R. Scheffold, Modern Synthetic Methods, Springer Verlag, Berlin, 1986, vol. 4, pp. 174-176
- (1986) Modern Synthetic Methods
- Seebach, D.¹ Imwinkelried, R.² Weber Ed., T.³

24
- 84986414946
- T. Weber R. Aeschimann T. Maetke D. Seebeach Helv. Chim. Acta 1986 69 1365
- (1986) Helv. Chim. Acta , vol.69 , pp. 1365
- Weber, T.¹ Aeschimann, R.² Maetke, T.³ Seebeach, D.⁴

25
- 0037055106
- Single point energies were obtained by ab initio calculations performed at the B·CYP/6-31G level for cis- 7 and trans- 11 of -2262.569254 au and -2262.567044 au, respectively
- N. A. Paras D. W. C. MacMillan J. Am. Chem. Soc. 2002 124 7894
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 7894
- Paras, N.A.¹ MacMillan, D.W.C.²

26
- 58849087131
- 10.1039/b814453b See, for instance:
- F. Alonso S. G. Davies A. S. Elend M. A. Leech P. M. Roberts A. D. Smith J. E. Thomson Org. Biomol. Chem. 2008 6 10.1039/b814453b
- (2008) Org. Biomol. Chem. , vol.6
- Alonso, F.¹ Davies, S.G.² Elend, A.S.³ Leech, M.A.⁴ Roberts, P.M.⁵ Smith, A.D.⁶ Thomson, J.E.⁷

27
- 33947487479
- M. Rosenblum A. K. Banerjee N. Danieli R. W. Fish V. Schlatter J. Am. Chem. Soc. 1963 85 316
- (1963) J. Am. Chem. Soc. , vol.85 , pp. 316
- Rosenblum, M.¹ Banerjee, A.K.² Danieli, N.³ Fish, R.W.⁴ Schlatter, V.⁵

28
- 0001230263
- The zero-point energies were obtained at HF/3-21G; see:
- U. T. Mueller-Westerhoff Z. Yang G. Ingram J. Organomet. Chem. 1993 463 163
- (1993) J. Organomet. Chem. , vol.463 , pp. 163
- Mueller-Westerhoff, U.T.¹ Yang, Z.² Ingram, G.³

29
- 0011083273
- A. P. Scott L. Radom J. Phys. Chem. 1996 100 16502
- (1996) J. Phys. Chem. , vol.100 , pp. 16502
- Scott, A.P.¹ Radom, L.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.