Reactions of glyoxal-derived iminium ions with unsaturated silyl and silyloxy reagents

Tetrahedron

Volumn 52, Issue 27, 1996, Pages 9079-9086

  Agami, Claude ^a   Bihan, Dominique ^a   Puchot Kadouri, Catherine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

MORPHOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030183278     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00450-4     Document Type: Article

References (17)

1. 1. Duthaler, R.O. Tetrahedron 1994, 50, 1539-1650. Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365-1399.
2. 1. Duthaler, R.O. Tetrahedron 1994, 50, 1539-1650. Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365-1399.
3. 2. See inter alia: Halinan, K.O.; Crout, D.H.G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. Griesbeck, A.G.; Hirt, J. Liebigs Ann. Chem. 1995, 1957-1961. Berkowitz, D.B.; Smith, M.K. Synthesis, 1996, 39-41. For α-ethynylglycine, see: Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Levecque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877-880. For a recent report about the synthesis of various unsaturated α-amino acids, see: Dunn, M.J.; Jackson, R.F.W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210-2215.
4. 2. See inter alia: Halinan, K.O.; Crout, D.H.G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. Griesbeck, A.G.; Hirt, J. Liebigs Ann. Chem. 1995, 1957-1961. Berkowitz, D.B.; Smith, M.K. Synthesis, 1996, 39-41. For α-ethynylglycine, see: Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Levecque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877-880. For a recent report about the synthesis of various unsaturated α-amino acids, see: Dunn, M.J.; Jackson, R.F.W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210-2215.
5. 2. See inter alia: Halinan, K.O.; Crout, D.H.G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. Griesbeck, A.G.; Hirt, J. Liebigs Ann. Chem. 1995, 1957-1961. Berkowitz, D.B.; Smith, M.K. Synthesis, 1996, 39-41. For α-ethynylglycine, see: Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Levecque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877-880. For a recent report about the synthesis of various unsaturated α-amino acids, see: Dunn, M.J.; Jackson, R.F.W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210-2215.
6. 2. See inter alia: Halinan, K.O.; Crout, D.H.G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. Griesbeck, A.G.; Hirt, J. Liebigs Ann. Chem. 1995, 1957-1961. Berkowitz, D.B.; Smith, M.K. Synthesis, 1996, 39-41. For α-ethynylglycine, see: Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Levecque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877-880. For a recent report about the synthesis of various unsaturated α-amino acids, see: Dunn, M.J.; Jackson, R.F.W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210-2215.
7. 2. See inter alia: Halinan, K.O.; Crout, D.H.G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. Griesbeck, A.G.; Hirt, J. Liebigs Ann. Chem. 1995, 1957-1961. Berkowitz, D.B.; Smith, M.K. Synthesis, 1996, 39-41. For α-ethynylglycine, see: Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Levecque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877-880. For a recent report about the synthesis of various unsaturated α-amino acids, see: Dunn, M.J.; Jackson, R.F.W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210-2215.
8. 3. Williams, R.M. Synthesis of Optically Active α-amino Acids; Pergamon: Oxford, 1989; pp. 287-289 and 293-295.
9. 4. Agami, C.; Couty, F.; Prince, B.; Puchot, C. Tetrahedron 1991, 47, 4343-4354.
10. 5. Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1-44.
11. For recent examples of this phenomenon, see: (a) Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc., Chem. Commun. 1993, 1542-1544.
12. (b) Agami, C.; Couty, F.; Lequesne, C. Tetrahedron 1995, 51, 4043-4056.
13. 6. Hosomi, A. Acc. Chem. Res. 1988, 21, 200-206. Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57-575.
14. 6. Hosomi, A. Acc. Chem. Res. 1988, 21, 200-206. Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57-575.
15. 7 Agami, C.; Couty, F.; Hamon, L.; Prince, B.; Puchot, C. Tetrahedron 1990, 46, 7003-7010.
16. 8. The X-ray analysis was performed by Dr. J. Vaissermann at the Laboratoire de Chimie des Métaux de Transition (Université P. et M. Curie).
17. 9. Agami, C.; Couty, F.; Poursoulis, M.; Vaissermann, J. Tetrahedron 1992, 48, 431-442.