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Volumn 66, Issue 26, 2001, Pages 8831-8842

Electrophilic fluorination of pyroglutamic acid derivatives: Application of substrate-dependent reactivity and diastereoselectivity to the synthesis of optically active 4-fluoroglutamic acids

(2) Konas, D W a Coward, J K a

a UNIVERSITY OF MICHIGAN (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHILIC FLUORINATIONS;

ACIDITY; SUBSTRATES; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

DERIVATIVES;

2 PYRROLIDONE DERIVATIVE; 4 FLUOROGLUTAMIC ACID; 4,4 DIFLUOROGLUTAMIC ACID; LACTAM DERIVATIVE; ORGANOFLUORINE DERIVATIVE; PYROGLUTAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIASTEREOISOMER; FLUORINATION; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

CHROMATOGRAPHY, THIN LAYER; FLUORINE; GLUTAMATES; INDICATORS AND REAGENTS; LACTAMS; MAGNETIC RESONANCE SPECTROSCOPY; PYRROLIDONECARBOXYLIC ACID; STEREOISOMERISM;

EID: 0035966190 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo0106804 Document Type: Article

Times cited : (43)

References (58)

1
- 0003907264
- Wiley: New York
- (1991) Fluorine in Bioorganic Chemistry
- Welch, J.T.¹ Eswarakrishnan, S.²

2
- 0003490830
- Elsevier: Amsterdam
- (1993) Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications
- Filler, R.¹ Kobayashi, Y.² Yagupolskii, L.M.³

3
- 0003416163
- Wiley: Chichester, West Sussex, England
- (1995) Fluorine-Containing Amino Acids, Synthesis and Properties
- Kukhar, V.P.¹ Soloshonok, V.A.²

4
- 0034353232
- (2000) Nat. Prod. Rep. , vol.17 , pp. 621
- Sutherland, A.¹ Willis, C.L.²

5
- 0001403860
- Ojima, I.; McCarthy, J. K., Welch, J. T., Eds.; American Chemical Society: Washington, D.C.
- (1996) Biomedical Frontiers of Fluorine Chemistry , pp. 118
- Tsukamoto, T.¹ Coward, J.K.² McGuire, J.J.³

6
- 0028978207
- (1995) Arch. Biochem. Biophys. , vol.321 , pp. 319
- McGuire, J.J.¹ Hart, B.P.² Haile, W.H.³ Rhee, M.⁴ Galivan, J.⁵ Coward, J.K.⁶

7
- 0030026396
- (1996) J. Med. Chem. , vol.39 , pp. 56
- Hart, B.P.¹ Haile, W.H.² Licato, N.J.³ Bolanowska, W.E.⁴ McGuire, J.J.⁵ Coward, J.K.⁶

8
- 0030052336
- (1996) J. Med. Chem. , vol.39 , pp. 66
- Tsukamoto, T.¹ Kitazume, T.² McGuire, J.J.³ Coward, J.K.⁴

9
- 0030601896
- (1996) Biochem. Pharmacol. , vol.52 , pp. 1295
- McGuire, J.J.¹ Hart, B.P.² Haile, W.H.³ Magee, K.J.⁴ Rhee, M.⁵ Bolanowska, W.E.⁶ Russell, C.⁷ Galivan, J.⁸ Paul, B.⁹ Coward, J.K.¹⁰

10
- 0001523313
- (1993) J. Fluorine Chem. , vol.60 , pp. 193
- Hudlicky, M.¹

11
- 0027164569
- (1993) Tetrahedron Lett. , vol.34 , pp. 4917
- Hart, B.P.¹ Coward, J.K.²

12
- 0020212110
- (1982) Int. J. Pept. Protein Res. , vol.20 , pp. 438
- Sufrin, J.R.¹ Balasubramanian, T.M.² Vora, C.M.³ Marshall, G.R.⁴

13
- 0032485422
- (1998) Tetrahedron Lett. , vol.39 , pp. 1169
- Demange, L.¹ Menez, A.² Dugave, C.³

14
- 2042438533
- Ph.D. Thesis, The University of Michigan, Ann Arbor
- (1995)
- Hart, B.P.¹

15
- 0000724689
- (1972) Can. J. Chem. , vol.50 , pp. 3129
- Lee, D.G.¹ Van den Engh, M.²

16
- 0007720410
- (1996) J. Phys. Org. Chem. , vol.9 , pp. 310
- Bakke, J.M.¹ Froehaug, A.E.²

17
- 0000468774
- (1996) Chem. Rev. , vol.96 , pp. 1737
- Lal, G.S.¹ Pez, G.P.² Syvret, R.G.³

18
- 0033595850
- (1999) Tetrahedron , vol.55 , pp. 12431
- Taylor, S.D.¹ Kotoris, C.C.² Hum, G.³

19
- 84988130722
- (1991) Synlett , pp. 187
- Differding, E.¹ Ofner, H.²

20
- 0041985571
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1019
- Brena-Valle, L.J.¹ Carreon Sanchez, R.² Cruz-Almanza, R.³

21
- 0029070832
- (1995) Tetrahedron , vol.51 , pp. 8545
- Del Bosco, M.¹ Johnstone, A.N.C.² Bazza, G.³ Lopatriello, S.⁴ North, M.⁵

22
- 2042437193
- note

23
- 0029811418
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1019
- Nakano, T.¹ Makino, M.² Morizawa, Y.³ Matsumura, Y.⁴

24
- 0033619849
- (1999) Org. Lett. , vol.1 , pp. 2105
- Konas, D.W.¹ Coward, J.K.²

25
- 0033972210
- (2000) J. Org. Chem. , vol.65 , pp. 263
- Jones, G.B.¹ Hynd, G.² Wright, J.M.³ Sharma, A.⁴

26
- 0000085980
- (1982) Tetrahedron Lett. , vol.23 , pp. 2641
- Koester, H.¹ Sinha, N.D.²

27
- 0001434147
- (2000) Tetrahedron Lett. , vol.41 , pp. 2817
- Lu, R.J.¹ Liu, D.P.² Giese, R.W.³

28
- 0000541005
- (2000) J. Org. Chem. , vol.65 , pp. 5077
- Hwu, J.R.¹ Jain, M.L.² Tsai, F.Y.³ Tsay, S.C.⁴ Balakumar, A.⁵ Hakimelahi, G.H.⁶

29
- 0000037765
- (1998) J. Org. Chem. , vol.63 , pp. 6021
- Wahlstrom, J.L.¹ Ronald, R.C.²

30
- 2042501831
- note

31
- 2042435892
- note

32
- 85008009593
- (1980) Chem. Pharm. Bull. , vol.28 , pp. 1449
- Saijo, S.¹ Wada, M.² Himizu, J.³ Ishida, A.⁴

33
- 0025072488
- (1990) J. Org. Chem. , vol.55 , pp. 3772
- Garner, P.¹ Park, J.M.²

34
- 0029829555
- (1996) Synthesis , pp. 1153
- De Nooy, A.E.J.¹ Besemer, A.C.² Van Bekkum, H.³

35
- 0029089082
- (1995) Carbohydr. Res. , vol.273 , pp. 249
- Li, K.¹ Helm, R.F.²

36
- 0000307530
- (1997) J. Org. Chem. , vol.62 , pp. 6974
- De Mico, A.¹ Margarita, R.² Parlanti, L.³ Vescovi, A.⁴ Piancatelli, G.⁵

37
- 0033534598
- (1999) J. Org. Chem. , vol.64 , pp. 293
- Epp, J.B.¹ Widlanski, T.S.²

38
- 0032560829
- (1998) Tetrahedron Lett. , vol.39 , pp. 5323
- Zhao, M.¹ Li, J.² Song, Z.³ Desmond, R.⁴ Tschaen, D.M.⁵ Grabowski, E.J.J.⁶ Reider, P.J.⁷

39
- 0026590329
- (1992) Tetrahedron Lett. , vol.33 , pp. 1509
- Avent, A.G.¹ Bowler, A.N.² Doyle, P.M.³ Marchand, C.M.⁴ Young, D.W.⁵

40
- 0028863323
- (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 3151
- Shin, C.G.¹ Nakamura, Y.² Yamada, Y.³ Yonezawa, Y.⁴ Umemura, K.⁵ Yoshimura, J.⁶

41
- 0000711059
- Wiley & Sons: New York; Collect
- (1990) Organic Syntheses , vol.7 , pp. 277-282
- Vedejs, E.¹ Larsen, S.²

42
- 0033578943
- (1999) J. Org. Chem. , vol.64 , pp. 7048
- Lal, G.S.¹ Pez, G.P.² Pesaresi, R.J.³ Prozonic, F.M.⁴ Cheng, H.S.⁵

43
- 0030959276
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 4565
- Meyers, A.I.¹ Seefeld, M.A.² Lefker, B.A.³ Blake, J.F.⁴

44
- 0033538331
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 5334
- Ando, K.¹ Green, N.S.² Li, Y.³ Houk, K.N.⁴

45
- 0034670608
- (2000) Tetrahedron , vol.56 , pp. 9843
- Groaning, M.D.¹ Meyers, A.I.²

46
- 0028044944
- (1994) J. Chem. Soc., Chem. Commun. , pp. 343
- Banks, R.E.¹ Lawrence, N.J.² Popplewell, A.L.³

47
- 0026034405
- (1991) Tetrahedron Lett. , vol.32 , pp. 1779
- Differding, E.¹ Ruegg, G.M.² Lang, R.W.³

48
- 0000498616
- (1981) J. Org. Chem. , vol.46 , pp. 4327
- Bordwell, F.G.¹ Fried, H.E.²

49
- 0007719617
- (1966) J. Am. Chem. Soc. , vol.88 , pp. 4761
- Adolph, H.G.¹ Kamlet, M.J.²

50
- 0000590650
- (1998) J. Org. Chem. , vol.63 , pp. 3937
- Castejon, H.J.¹ Wiberg, K.B.²

51
- 0034731617
- (2000) J. Org. Chem. , vol.65 , pp. 8970
- Behnam, S.M.¹ Behnam, S.E.² Ando, K.³ Green, N.S.⁴ Houk, K.N.⁵

52
- 2042506497
- Unpublished results
- Konas, D.W.¹

53
- 0003463819
- Wiley; New York, N.Y.
- (2000) The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Materials Science
- Greenberg, A.¹ Breneman, C.M.² Libman, J.F.³

54
- 0028305274
- (1994) Nucleosides Nucleotides , vol.13 , pp. 1493
- Pickering, L.¹ Malhi, B.S.² Coe, P.L.³ Walker, R.T.⁴

55
- 0026705590
- (1992) Chem. Pharm. Bull. , vol.40 , pp. 1925
- Ikota, N.¹

56
- 0029102387
- (1995) J. Med. Chem. , vol.38 , pp. 2866
- Olson, G.L.¹ Cheung, H.-C.² Chiang, E.³ Madison, V.S.⁴ Sepinwall, J.⁵ Vincent, G.P.⁶ Winokur, A.⁷ Gary, K.A.⁸

57
- 2042540161
- note

58
- 2042509146
- note

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