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Volumn 86, Issue 6, 2003, Pages 1852-1861

Enantioselective preparation of 2-aminomethyl carboxylic acid derivatives: Solving the β2-amino acid problem with the chiral auxiliary 4-isopropyl-5,5-diphenyloxazolidin-2-one (DIOZ)

(12) Seebach, Dieter a Schaeffer, Laurent a Gessier, François a Bindschädler, Pascal a Jäger, Corinna a Josien, Delphine a Kopp, Sascha a Lelais, Gérald a Mahajan, Yogesh R a Micuch, Peter a Sebesta, Radovan a Schweizer, Bernd W a

a ETH ZURICH (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CARBOXYLIC ACIDS; CRYSTALLINE MATERIALS; KETONES; STEREOCHEMISTRY;

ENANTIOSELECTIVE PREPARATION;

AMINO ACIDS;

2 AMINOMETHYL CARBOXYLIC ACID DERIVATIVE; 4 ISOPROPYL 5,5 DIPHENYLOXAZOLIDIN 2 ONE; BETA AMINO ACID; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL CELL; ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; DERIVATIZATION; DNA HELIX; ENANTIOSELECTIVITY; METHYLATION; NONHUMAN; PEPTIDE ANALYSIS; PRIORITY JOURNAL; PROTEIN SECONDARY STRUCTURE; X RAY CRYSTALLOGRAPHY;

EID: 0042305011 PISSN: 0018019X EISSN: None Source Type: Journal
DOI: 10.1002/hlca.200390149 Document Type: Article

Times cited : (49)

References (37)

1
- 0029953285
- a) D. Seebach, M. Overhand, F. N. M. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913;
- (1996) Helv. Chim. Acta , vol.79 , pp. 913
- Seebach, D.¹ Overhand, M.² Kühnle, F.N.M.³ Martinoni, B.⁴ Oberer, L.⁵ Hommel, U.⁶ Widmer, H.⁷

2
- 0029856721
- b) D. Seebach, P. E. Ciceri, M. Overhand, B. Jaun, D. Rigo, L. Oberer, U. Hommel, R. Amstutz, H. Widmer, Helv. Chim. Acta 1986, 79, 2043;
- (1986) Helv. Chim. Acta , vol.79 , pp. 2043
- Seebach, D.¹ Ciceri, P.E.² Overhand, M.³ Jaun, B.⁴ Rigo, D.⁵ Oberer, L.⁶ Hommel, U.⁷ Amstutz, R.⁸ Widmer, H.⁹

3
- 0001452530
- c) D. Seebach, S. Abele, K. Gademann, G. Guichard, T. Hintermann, B. Jaun, J. L. Matthews, J. V. Schreiber, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1998, 81, 932;
- (1998) Helv. Chim. Acta , vol.81 , pp. 932
- Seebach, D.¹ Abele, S.² Gademann, K.³ Guichard, G.⁴ Hintermann, T.⁵ Jaun, B.⁶ Matthews, J.L.⁷ Schreiber, J.V.⁸ Oberer, L.⁹ Hommel, U.¹⁰ Widmer, H.¹¹

4
- 0034806777
- d) X. Daura, K. Gademann, H. Schäfer, B. Jaun, D. Seebach, W. F. van Gunsteren, J. Am. Chem. Soc. 2001, 123, 2393.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 2393
- Daura, X.¹ Gademann, K.² Schäfer, H.³ Jaun, B.⁴ Seebach, D.⁵ Van Gunsteren, W.F.⁶

5
- 0001034344
- D. Seebach, S. Abele, K. Gademann, B. Jaun, Angew. Chem. 1999, 111, 1700; Angew. Chem., Int. Ed. 1994, 38, 1595.
- (1999) Angew. Chem. , vol.111 , pp. 1700
- Seebach, D.¹ Abele, S.² Gademann, K.³ Jaun, B.⁴

6
- 0043041038
- D. Seebach, S. Abele, K. Gademann, B. Jaun, Angew. Chem. 1999, 111, 1700; Angew. Chem., Int. Ed. 1994, 38, 1595.
- (1994) Angew. Chem., Int. Ed. , vol.38 , pp. 1595

7
- 0035382627
- J. Frackenpohl, P. I. Arvidsson, J. V. Schreiber, D. Seebach, ChemBioChem 2001, 2, 445.
- (2001) ChemBioChem , vol.2 , pp. 445
- Frackenpohl, J.¹ Arvidsson, P.I.² Schreiber, J.V.³ Seebach, D.⁴

8
- 0036737771
- H. Wiegand, B. Wirz, A. Schweitzer, G. P. Camenisch, M. I. Rodriguez Perez, G. Gross, R. Woessner, R. Voges, P. I. Arvidsson, J. Frackenpohl, D. Seebach, Biopharm. Drug Dispos. 2002, 23, 251.
- (2002) Biopharm. Drug Dispos. , vol.23 , pp. 251
- Wiegand, H.¹ Wirz, B.² Schweitzer, A.³ Camenisch, G.P.⁴ Rodriguez Perez, M.I.⁵ Gross, G.⁶ Woessner, R.⁷ Voges, R.⁸ Arvidsson, P.I.⁹ Frackenpohl, J.¹⁰ Seebach, D.¹¹

9
- 0036903966
- J. V. Schreiber, J. Frackenpohl, F. Moser, T. Fleischmann, H.-P. Kohler, D. Seebach, ChemBioChem 2002, 3, 424.
- (2002) ChemBioChem , vol.3 , pp. 424
- Schreiber, J.V.¹ Frackenpohl, J.² Moser, F.³ Fleischmann, T.⁴ Kohler, H.-P.⁵ Seebach, D.⁶

10
- 0032881267
- M. Werder, H. Hauser, S. Abele, D. Seebach, Helv. Chim. Acta 1999, 82, 1774; K. Gademann, T. Kimmerlin, D. Hoyer, D. Seebach, J. Med. Chem. 2001, 44, 2460; C. Nunn, M. Rueping, D. Langenegger, E. Schuepbach, T. Kimmerlin, P. Micuch, K. Hurth, D. Seebach, D. Hoyer, Naunyn-Schmiedeberg's Arch. Pharmacol. 2003, 367, 95.
- (1999) Helv. Chim. Acta , vol.82 , pp. 1774
- Werder, M.¹ Hauser, H.² Abele, S.³ Seebach, D.⁴

11
- 0035913057
- M. Werder, H. Hauser, S. Abele, D. Seebach, Helv. Chim. Acta 1999, 82, 1774; K. Gademann, T. Kimmerlin, D. Hoyer, D. Seebach, J. Med. Chem. 2001, 44, 2460; C. Nunn, M. Rueping, D. Langenegger, E. Schuepbach, T. Kimmerlin, P. Micuch, K. Hurth, D. Seebach, D. Hoyer, Naunyn-Schmiedeberg's Arch. Pharmacol. 2003, 367, 95.
- (2001) J. Med. Chem. , vol.44 , pp. 2460
- Gademann, K.¹ Kimmerlin, T.² Hoyer, D.³ Seebach, D.⁴

12
- 0037292238
- M. Werder, H. Hauser, S. Abele, D. Seebach, Helv. Chim. Acta 1999, 82, 1774; K. Gademann, T. Kimmerlin, D. Hoyer, D. Seebach, J. Med. Chem. 2001, 44, 2460; C. Nunn, M. Rueping, D. Langenegger, E. Schuepbach, T. Kimmerlin, P. Micuch, K. Hurth, D. Seebach, D. Hoyer, Naunyn-Schmiedeberg's Arch. Pharmacol. 2003, 367, 95.
- (2003) Naunyn-Schmiedeberg's Arch. Pharmacol. , vol.367 , pp. 95
- Nunn, C.¹ Rueping, M.² Langenegger, D.³ Schuepbach, E.⁴ Kimmerlin, T.⁵ Micuch, P.⁶ Hurth, K.⁷ Seebach, D.⁸ Hoyer, D.⁹

13
- 0036523467
- M. Rueping, Y. Mahajan, M. Sauer, D. Seebach, ChemBioChem 2002, 257; N. Umezawa, M. A. Gelman, M. C. Haigis, R. T. Raines, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 368; C. Garcia-Echeverria, S. Ruetz, Bioorg. Med. Chem. Lett. 2003, 13, 247.
- (2002) ChemBioChem , pp. 257
- Rueping, M.¹ Mahajan, Y.² Sauer, M.³ Seebach, D.⁴

14
- 0037160363
- M. Rueping, Y. Mahajan, M. Sauer, D. Seebach, ChemBioChem 2002, 257; N. Umezawa, M. A. Gelman, M. C. Haigis, R. T. Raines, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 368; C. Garcia-Echeverria, S. Ruetz, Bioorg. Med. Chem. Lett. 2003, 13, 247.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 368
- Umezawa, N.¹ Gelman, M.A.² Haigis, M.C.³ Raines, R.T.⁴ Gellman, S.H.⁵

15
- 0037212777
- M. Rueping, Y. Mahajan, M. Sauer, D. Seebach, ChemBioChem 2002, 257; N. Umezawa, M. A. Gelman, M. C. Haigis, R. T. Raines, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 368; C. Garcia-Echeverria, S. Ruetz, Bioorg. Med. Chem. Lett. 2003, 13, 247.
- (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 247
- Garcia-Echeverria, C.¹ Ruetz, S.²

16
- 0036397712
- M. Rueping, J. V. Schreiber, G. Lelais, B. Jaun, D. Seebach, Helv. Chim. Acta 2002, 85, 2577.
- (2002) Helv. Chim. Acta , vol.85 , pp. 2577
- Rueping, M.¹ Schreiber, J.V.² Lelais, G.³ Jaun, B.⁴ Seebach, D.⁵

17
- 0035091757
- a) D. Seebach, J. V. Schreiber, P. I. Arvidsson, J. Frackenpohl, Helv. Chim. Acta 2001, 84, 271;
- (2001) Helv. Chim. Acta , vol.84 , pp. 271
- Seebach, D.¹ Schreiber, J.V.² Arvidsson, P.I.³ Frackenpohl, J.⁴

18
- 0036293874
- b) T. Kimmerlin, D. Seebach, D. Hilvert, Helv. Chem. Acta 2002, 85, 1812;
- (2002) Helv. Chem. Acta , vol.85 , pp. 1812
- Kimmerlin, T.¹ Seebach, D.² Hilvert, D.³

19
- 0037010015
- c) R. P. Cheng, W. F. DeGrado, J. Am. Chem. Soc. 2002, 124, 11564;
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 11564
- Cheng, R.P.¹ DeGrado, W.F.²

20
- 0038411295
- d) P. I. Arvidsson, J. Frackenpohl, D. Seebach, Helv. Chim. Acta 2003, 86, 1522.
- (2003) Helv. Chim. Acta , vol.86 , pp. 1522
- Arvidsson, P.I.¹ Frackenpohl, J.² Seebach, D.³

21
- 0037201534
- M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991.
- (2002) Tetrahedron , vol.58 , pp. 7991
- Liu, M.¹ Sibi, M.P.²

22
- 84958315401
- D. A. Evans, D. L. Rieger, M. T. Bilodeau, F. Urpi, J. Am. Chem. Soc. 1991, 113, 1047.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 1047
- Evans, D.A.¹ Rieger, D.L.² Bilodeau, M.T.³ Urpi, F.⁴

23
- 0031759777
- T. Hintermann, D. Seebach, Helv. Chim. Acta 1998, 81, 2093.
- (1998) Helv. Chim. Acta , vol.81 , pp. 2093
- Hintermann, T.¹ Seebach, D.²

24
- 0036293584
- C. Gaul, B. W. Schweizer, P. Seiler, D. Seebach, Helv. Chim. Acta 2002, 85, 1546.
- (2002) Helv. Chim. Acta , vol.85 , pp. 1546
- Gaul, C.¹ Schweizer, B.W.² Seiler, P.³ Seebach, D.⁴

25
- 0000193384
- T. Hintermann, D. Seebach, Synlett 1997, 437; D. Seebach, K. Gademann, J. V. Schreiber, J. L. Matthews, T. Hintermann, B. Jaun, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1997, 80, 2033; D. Seebach, M. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger, D. Hoyer, Helv. Chim. Acta 2001, 84, 3503; P. Micuch, D. Seebach, Helv. Chim. Acta 2002, 85, 1567.
- (1997) Synlett , pp. 437
- Hintermann, T.¹ Seebach, D.²

26
- 0001280157
- T. Hintermann, D. Seebach, Synlett 1997, 437; D. Seebach, K. Gademann, J. V. Schreiber, J. L. Matthews, T. Hintermann, B. Jaun, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1997, 80, 2033; D. Seebach, M. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger, D. Hoyer, Helv. Chim. Acta 2001, 84, 3503; P. Micuch, D. Seebach, Helv. Chim. Acta 2002, 85, 1567.
- (1997) Helv. Chim. Acta , vol.80 , pp. 2033
- Seebach, D.¹ Gademann, K.² Schreiber, J.V.³ Matthews, J.L.⁴ Hintermann, T.⁵ Jaun, B.⁶ Oberer, L.⁷ Hommel, U.⁸ Widmer, H.⁹

27
- 0035218046
- T. Hintermann, D. Seebach, Synlett 1997, 437; D. Seebach, K. Gademann, J. V. Schreiber, J. L. Matthews, T. Hintermann, B. Jaun, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1997, 80, 2033; D. Seebach, M. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger, D. Hoyer, Helv. Chim. Acta 2001, 84, 3503; P. Micuch, D. Seebach, Helv. Chim. Acta 2002, 85, 1567.
- (2001) Helv. Chim. Acta , vol.84 , pp. 3503
- Seebach, D.¹ Rueping, M.² Arvidsson, P.I.³ Kimmerlin, T.⁴ Micuch, P.⁵ Noti, C.⁶ Langenegger, D.⁷ Hoyer, D.⁸

28
- 0036296775
- T. Hintermann, D. Seebach, Synlett 1997, 437; D. Seebach, K. Gademann, J. V. Schreiber, J. L. Matthews, T. Hintermann, B. Jaun, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1997, 80, 2033; D. Seebach, M. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger, D. Hoyer, Helv. Chim. Acta 2001, 84, 3503; P. Micuch, D. Seebach, Helv. Chim. Acta 2002, 85, 1567.
- (2002) Helv. Chim. Acta , vol.85 , pp. 1567
- Micuch, P.¹ Seebach, D.²

29
- 0035932591
- M. Brewer, D. H. Rich, Org. Lett. 2001, 3, 945.
- (2001) Org. Lett. , vol.3 , pp. 945
- Brewer, M.¹ Rich, D.H.²

30
- 0033588390
- D. A. Evans, L. D. Wu, J. J. M. Wiener, J. S. Johnson, D. H. B. Ripin, J. S. Tedrow, J. Org. Chem. 1999, 64, 6411.
- (1999) J. Org. Chem. , vol.64 , pp. 6411
- Evans, D.A.¹ Wu, L.D.² Wiener, J.J.M.³ Johnson, J.S.⁴ Ripin, D.H.B.⁵ Tedrow, J.S.⁶

31
- 0027536014
- T. Tsunoda, Y. Yamamiya, S. Ito, Tetrahedron Lett. 1993, 34, 1639.
- (1993) Tetrahedron Lett. , vol.34 , pp. 1639
- Tsunoda, T.¹ Yamamiya, Y.² Ito, S.³

32
- 0027579802
- O. Kanie, S. C. Crawley, M. M. Palcic, O. Hindsgaul, Carbohydrate Res. 1993, 243, 139.
- (1993) Carbohydrate Res. , vol.243 , pp. 139
- Kanie, O.¹ Crawley, S.C.² Palcic, M.M.³ Hindsgaul, O.⁴

33
- 0000761191
- Ed. R. Adams, John Wiley, New York
- H. Wolff, in 'Organic Reactions', Vol. 3, Ed. R. Adams, John Wiley, New York, 1946, p. 307-336.
- (1946) Organic Reactions , vol.3 , pp. 307-336
- Wolff, H.¹

34
- 0042039376
- P. G. Reddy, T. V. Pratap, G. D. K. Kumar, S. K. Mohanty, S. Baskaran, Eur. J. Org. Chem. 2002, 3740.
- (2002) Eur. J. Org. Chem. , pp. 3740
- Reddy, P.G.¹ Pratap, T.V.² Kumar, G.D.K.³ Mohanty, S.K.⁴ Baskaran, S.⁵

35
- 0003803058
- Springer Verlag
- M. Bodanszky, A. Bodanszky, 'The Practice of Peptide Synthesis', 2nd edn. Springer Verlag 1994, 48.
- (1994) The Practice of Peptide Synthesis, 2nd Edn. , pp. 48
- Bodanszky, M.¹ Bodanszky, A.²

36
- 0032555004
- A. F. Abdel-Magid, J. H. Cohen, C. A. Maryanoff, R. D. Shah, F. J. Villani, F. Zhang, Tetrahedron Lett. 1998, 39, 3391.
- (1998) Tetrahedron Lett. , vol.39 , pp. 3391
- Abdel-Magid, A.F.¹ Cohen, J.H.² Maryanoff, C.A.³ Shah, R.D.⁴ Villani, F.J.⁵ Zhang, F.⁶

37
- 0001310463
- M. Orfanopoulos, I. Smonou, Synth. Commun. 1988, 18, 833.
- (1988) Synth. Commun. , vol.18 , pp. 833
- Orfanopoulos, M.¹ Smonou, I.²

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