Stereocontrolled synthesis of α,α-disubstituted α-aminoaldehydes and α-aminoacids using a [3,3] allylic trichloracetimidate rearrangement

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2573-2576

  Imogaï, Hassan ^a   Petit, Yves ^a   Larchevêque, Marc ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AMINOALDEHYDE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029926328     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00393-0     Document Type: Article

References (39)

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6. Mutter, M. Angew. Chem. Int. Ed. Engl. 1985, 97, 639-653; Toniolo, C. CRC Critical Rev. Biochem. 1980, 9, 1-44; Karle, I.L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; Benedetti, E.; Toniolo, C.; Hardy, P.; Barone, V.; Bavoso, B.; di Blasio, B.; Grimaldi, P.; Lelj, F.; Pavone, V.; Pedone, C.; Bonora, G.M.; Lingham, I. J. Am. Chem. Soc. 1984, 106, 8146-8152; Crisma, M.; Valle, G.; Bonora, G.M.; Toniolo, C.; Lelj, F.; Barone, V.; Fraternali, F.; Hardy, P.M.; Maia, H.L.S. Biopolymers 1991, 31, 637-641.
7. Mutter, M. Angew. Chem. Int. Ed. Engl. 1985, 97, 639-653; Toniolo, C. CRC Critical Rev. Biochem. 1980, 9, 1-44; Karle, I.L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; Benedetti, E.; Toniolo, C.; Hardy, P.; Barone, V.; Bavoso, B.; di Blasio, B.; Grimaldi, P.; Lelj, F.; Pavone, V.; Pedone, C.; Bonora, G.M.; Lingham, I. J. Am. Chem. Soc. 1984, 106, 8146-8152; Crisma, M.; Valle, G.; Bonora, G.M.; Toniolo, C.; Lelj, F.; Barone, V.; Fraternali, F.; Hardy, P.M.; Maia, H.L.S. Biopolymers 1991, 31, 637-641.
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9. For overviews, see Williams, R.M. Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford, 1989; Heimgartner, H. Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264. For recent synthesis, see: Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarten, H.; Stierli, F. Helv. Chem. Acta 1992, 75, 1666-1696; Colson, P.J.; Hegedus, L.S. J. Org. Chem. 1993, 58, 5918-5924; Cativiela, C.; Diaz-de-Villegas, M.D.; Galvez, J.A. Tetrahedron-Asymmetry 1994, 5, 261-268; Berkowitz, D.B.; Smith, M.K. J. Org. Chem. 1995, 60, 1233-1238; Jung, M.E.; D'Amico, D.C. J. Am. Chem. Soc. 1995, 117, 7379-7388.
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13. For overviews, see Williams, R.M. Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford, 1989; Heimgartner, H. Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264. For recent synthesis, see: Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarten, H.; Stierli, F. Helv. Chem. Acta 1992, 75, 1666-1696; Colson, P.J.; Hegedus, L.S. J. Org. Chem. 1993, 58, 5918-5924; Cativiela, C.; Diaz-de-Villegas, M.D.; Galvez, J.A. Tetrahedron-Asymmetry 1994, 5, 261-268; Berkowitz, D.B.; Smith, M.K. J. Org. Chem. 1995, 60, 1233-1238; Jung, M.E.; D'Amico, D.C. J. Am. Chem. Soc. 1995, 117, 7379-7388.
14. For overviews, see Williams, R.M. Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford, 1989; Heimgartner, H. Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264. For recent synthesis, see: Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarten, H.; Stierli, F. Helv. Chem. Acta 1992, 75, 1666-1696; Colson, P.J.; Hegedus, L.S. J. Org. Chem. 1993, 58, 5918-5924; Cativiela, C.; Diaz-de-Villegas, M.D.; Galvez, J.A. Tetrahedron-Asymmetry 1994, 5, 261-268; Berkowitz, D.B.; Smith, M.K. J. Org. Chem. 1995, 60, 1233-1238; Jung, M.E.; D'Amico, D.C. J. Am. Chem. Soc. 1995, 117, 7379-7388.
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30. 3= Ph)
31. 5c. Yields in purified products (after a rapid chromatography on carbonated silica gel) were in all cases better than 95%.
32. Thermal rearrangements were performed by refluxing trichloracetimidates in xylene for 4 to 10 hours. Yields %: 6a: 98; 6b: 62; 6c: 60; 6d: 70.
33. In all cases, the stereochemistry of the double bond was purely E.
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36. 2), 98%.
37. 2)
38. 2O) for the S acid: Kolb, M.; Barth, J. Angew. Chem. Int. Ed. Engl 1980, 19, 725-726.
39. The enantiomeric purities were measured on a β-cyclodextrin stationary phase: Cydex-B from SGE (50 m) for the aldehydes 7 isolated after flash-chromatography and by NMR in the presence of tris[3-(heptafluoropropylhydroxymethylene)-d-camphorato]europium III for the esters 8. They were found better than 98%.