Stereospecific synthesis of chiral alkinylogous amino acids

Chemical Communications

Volumn , Issue 6, 1996, Pages 733-734

  Reetz, Manfred T ^a   Strack, Thomas J ^a   Kanand, Jürgen ^a   Goddard, Richard ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKINYLOGOUS AMINO ACID; AMINO ACID; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOSPECIFICITY;

EID: 0029919355     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000733     Document Type: Article

References (22)

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2. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989; M. T. Reetz, Angew. Chem., 1991, 103, 1559; Angew. Chem., Int. Ed. Engl., 1991, 30, 1531; P. Cintas, Tetrahedron, 1991, 47, 6079; K. Drauz, A. Kleemann and J. Martens, Angew. Chem., 1982, 94, 590; Angew. Chem., Int. Ed. Engl., 1982, 21, 584.
3. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989; M. T. Reetz, Angew. Chem., 1991, 103, 1559; Angew. Chem., Int. Ed. Engl., 1991, 30, 1531; P. Cintas, Tetrahedron, 1991, 47, 6079; K. Drauz, A. Kleemann and J. Martens, Angew. Chem., 1982, 94, 590; Angew. Chem., Int. Ed. Engl., 1982, 21, 584.
4. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989; M. T. Reetz, Angew. Chem., 1991, 103, 1559; Angew. Chem., Int. Ed. Engl., 1991, 30, 1531; P. Cintas, Tetrahedron, 1991, 47, 6079; K. Drauz, A. Kleemann and J. Martens, Angew. Chem., 1982, 94, 590; Angew. Chem., Int. Ed. Engl., 1982, 21, 584.
5. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989; M. T. Reetz, Angew. Chem., 1991, 103, 1559; Angew. Chem., Int. Ed. Engl., 1991, 30, 1531; P. Cintas, Tetrahedron, 1991, 47, 6079; K. Drauz, A. Kleemann and J. Martens, Angew. Chem., 1982, 94, 590; Angew. Chem., Int. Ed. Engl., 1982, 21, 584.
6. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989; M. T. Reetz, Angew. Chem., 1991, 103, 1559; Angew. Chem., Int. Ed. Engl., 1991, 30, 1531; P. Cintas, Tetrahedron, 1991, 47, 6079; K. Drauz, A. Kleemann and J. Martens, Angew. Chem., 1982, 94, 590; Angew. Chem., Int. Ed. Engl., 1982, 21, 584.
7. A. Giannis and T. Kolter, Angew. Chem., 1993, 105, 1303; Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; H. Kessler, A. Geyer, H. Matter and M. Köck, Int. J. Peptide Protein Res., 1992, 40, 25; R. Hirschmann, Angew. Chem., 1991, 103, 1305; Angew. Chem., int. Ed. Engl., 1991, 30, 1278; G. Holzemann, Kontakte (Darmstadt), 1991(1), 3 and 1991(2), 55; M. T. Reetz, N. Griebenow and R. Goddard, J. Chem. Soc., Chem. Commun., 1995, 1605.
8. A. Giannis and T. Kolter, Angew. Chem., 1993, 105, 1303; Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; H. Kessler, A. Geyer, H. Matter and M. Köck, Int. J. Peptide Protein Res., 1992, 40, 25; R. Hirschmann, Angew. Chem., 1991, 103, 1305; Angew. Chem., int. Ed. Engl., 1991, 30, 1278; G. Holzemann, Kontakte (Darmstadt), 1991(1), 3 and 1991(2), 55; M. T. Reetz, N. Griebenow and R. Goddard, J. Chem. Soc., Chem. Commun., 1995, 1605.
9. A. Giannis and T. Kolter, Angew. Chem., 1993, 105, 1303; Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; H. Kessler, A. Geyer, H. Matter and M. Köck, Int. J. Peptide Protein Res., 1992, 40, 25; R. Hirschmann, Angew. Chem., 1991, 103, 1305; Angew. Chem., int. Ed. Engl., 1991, 30, 1278; G. Holzemann, Kontakte (Darmstadt), 1991(1), 3 and 1991(2), 55; M. T. Reetz, N. Griebenow and R. Goddard, J. Chem. Soc., Chem. Commun., 1995, 1605.
10. A. Giannis and T. Kolter, Angew. Chem., 1993, 105, 1303; Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; H. Kessler, A. Geyer, H. Matter and M. Köck, Int. J. Peptide Protein Res., 1992, 40, 25; R. Hirschmann, Angew. Chem., 1991, 103, 1305; Angew. Chem., int. Ed. Engl., 1991, 30, 1278; G. Holzemann, Kontakte (Darmstadt), 1991(1), 3 and 1991(2), 55; M. T. Reetz, N. Griebenow and R. Goddard, J. Chem. Soc., Chem. Commun., 1995, 1605.
11. A. Giannis and T. Kolter, Angew. Chem., 1993, 105, 1303; Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; H. Kessler, A. Geyer, H. Matter and M. Köck, Int. J. Peptide Protein Res., 1992, 40, 25; R. Hirschmann, Angew. Chem., 1991, 103, 1305; Angew. Chem., int. Ed. Engl., 1991, 30, 1278; G. Holzemann, Kontakte (Darmstadt), 1991(1), 3 and 1991(2), 55; M. T. Reetz, N. Griebenow and R. Goddard, J. Chem. Soc., Chem. Commun., 1995, 1605.
12. A. Giannis and T. Kolter, Angew. Chem., 1993, 105, 1303; Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; H. Kessler, A. Geyer, H. Matter and M. Köck, Int. J. Peptide Protein Res., 1992, 40, 25; R. Hirschmann, Angew. Chem., 1991, 103, 1305; Angew. Chem., int. Ed. Engl., 1991, 30, 1278; G. Holzemann, Kontakte (Darmstadt), 1991(1), 3 and 1991(2), 55; M. T. Reetz, N. Griebenow and R. Goddard, J. Chem. Soc., Chem. Commun., 1995, 1605.
13. A. Giannis and T. Kolter, Angew. Chem., 1993, 105, 1303; Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; H. Kessler, A. Geyer, H. Matter and M. Köck, Int. J. Peptide Protein Res., 1992, 40, 25; R. Hirschmann, Angew. Chem., 1991, 103, 1305; Angew. Chem., int. Ed. Engl., 1991, 30, 1278; G. Holzemann, Kontakte (Darmstadt), 1991(1), 3 and 1991(2), 55; M. T. Reetz, N. Griebenow and R. Goddard, J. Chem. Soc., Chem. Commun., 1995, 1605.
14. A. Giannis and T. Kolter, Angew. Chem., 1993, 105, 1303; Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; H. Kessler, A. Geyer, H. Matter and M. Köck, Int. J. Peptide Protein Res., 1992, 40, 25; R. Hirschmann, Angew. Chem., 1991, 103, 1305; Angew. Chem., int. Ed. Engl., 1991, 30, 1278; G. Holzemann, Kontakte (Darmstadt), 1991(1), 3 and 1991(2), 55; M. T. Reetz, N. Griebenow and R. Goddard, J. Chem. Soc., Chem. Commun., 1995, 1605.
15. K. Angermund, unpublished results.
16. Racemic forms of the amides of alkinylogous amino acids have been reported in the patent literature: A. G. Doutheau, J. Gore and G. Quash, Eur. Pat. Appl., EP 133 407; Chem. Abst., 1985, 103, 22 170c.
17. Racemic forms of the amides of alkinylogous amino acids have been reported in the patent literature: A. G. Doutheau, J. Gore and G. Quash, Eur. Pat. Appl., EP 133 407; Chem. Abst., 1985, 103, 22 170c.
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