The tetrahydrooxazinone way to enantiopure α-amino acids: Synthesis of cis and trans 3-vinyl pipecolic acids via an intramolecular reaction between an iminium ion and an allylsilane moieties

Tetrahedron

Volumn 54, Issue 35, 1998, Pages 10309-10316

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

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 VINYLPIPECOLIC ACID METHYL ESTER; ALPHA AMINO ACID; GLYOXAL; IMINE; PHENYLGLYCINE; PIPECOLIC ACID DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032572846     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00486-4     Document Type: Article

References (18)

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2. 1. Hiemstra, H.; Speckamp, W.N. in Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., (Eds.); Pergamon Press, Oxford 1991; Vol. 2, pp. 1047-1082. Overman, L.E.; Ricca, D.J. in Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., (Eds.); Pergamon Press, Oxford 1991; Vol. 2, pp. 975-1006.
3. 2 For some recent reports in this field, see: Ofial, A.R.; Mayr, H. J. Org. Chem. 1996, 67, 5823. Khim, S.K.; Wu, X.; Mariano, P.S. Tetrahedron Lett. 1996, 37, 571. Burgess, L.E.; Gross, E.K.M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255-3258. Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627. Luker, T.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1997, 62, 3592. Ofial, A.R.; Mayr, H. Liebigs Ann./Recueil 1997, 333-335.
4. 2 For some recent reports in this field, see: Ofial, A.R.; Mayr, H. J. Org. Chem. 1996, 67, 5823. Khim, S.K.; Wu, X.; Mariano, P.S. Tetrahedron Lett. 1996, 37, 571. Burgess, L.E.; Gross, E.K.M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255-3258. Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627. Luker, T.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1997, 62, 3592. Ofial, A.R.; Mayr, H. Liebigs Ann./Recueil 1997, 333-335.
5. 2 For some recent reports in this field, see: Ofial, A.R.; Mayr, H. J. Org. Chem. 1996, 67, 5823. Khim, S.K.; Wu, X.; Mariano, P.S. Tetrahedron Lett. 1996, 37, 571. Burgess, L.E.; Gross, E.K.M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255-3258. Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627. Luker, T.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1997, 62, 3592. Ofial, A.R.; Mayr, H. Liebigs Ann./Recueil 1997, 333-335.
6. 2 For some recent reports in this field, see: Ofial, A.R.; Mayr, H. J. Org. Chem. 1996, 67, 5823. Khim, S.K.; Wu, X.; Mariano, P.S. Tetrahedron Lett. 1996, 37, 571. Burgess, L.E.; Gross, E.K.M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255-3258. Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627. Luker, T.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1997, 62, 3592. Ofial, A.R.; Mayr, H. Liebigs Ann./Recueil 1997, 333-335.
7. 2 For some recent reports in this field, see: Ofial, A.R.; Mayr, H. J. Org. Chem. 1996, 67, 5823. Khim, S.K.; Wu, X.; Mariano, P.S. Tetrahedron Lett. 1996, 37, 571. Burgess, L.E.; Gross, E.K.M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255-3258. Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627. Luker, T.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1997, 62, 3592. Ofial, A.R.; Mayr, H. Liebigs Ann./Recueil 1997, 333-335.
8. 2 For some recent reports in this field, see: Ofial, A.R.; Mayr, H. J. Org. Chem. 1996, 67, 5823. Khim, S.K.; Wu, X.; Mariano, P.S. Tetrahedron Lett. 1996, 37, 571. Burgess, L.E.; Gross, E.K.M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255-3258. Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627. Luker, T.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem. 1997, 62, 3592. Ofial, A.R.; Mayr, H. Liebigs Ann./Recueil 1997, 333-335.
9. 3 Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079-9086.
10. 4 Preliminary communication: Agami, C.; Bihan, D.; Morgentin, R.; Puchot-Kadouri, C. Synlett 1997, 799-800.
11. 5 Duthaler, R.O. Tetrahedron 1994, 50, 1539-1650.
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14. 8 For an analogous intramolecular nucleophilic attack onto a transient vinylic carbocation generated from a propargyl silane, see: Esch, P.M.; Hiemstra, H.; Speckamp, N. Tetrahedron Lett. 1988, 29, 367.
15. 9 Agami, C.; Couty, F.; Prince, B.; Puchot, C. Tetrahedron 1991, 47, 4343-4354. Agami, C.; Couty, F.; Poursoulis, M.; Vaissermann Tetrahedron 1992, 48, 431-442. Agami, C.; Cases, M.; Couty, F. J. Org. Chem. 1994, 59, 7937-7940.
16. 9 Agami, C.; Couty, F.; Prince, B.; Puchot, C. Tetrahedron 1991, 47, 4343-4354. Agami, C.; Couty, F.; Poursoulis, M.; Vaissermann Tetrahedron 1992, 48, 431-442. Agami, C.; Cases, M.; Couty, F. J. Org. Chem. 1994, 59, 7937-7940.
17. 9 Agami, C.; Couty, F.; Prince, B.; Puchot, C. Tetrahedron 1991, 47, 4343-4354. Agami, C.; Couty, F.; Poursoulis, M.; Vaissermann Tetrahedron 1992, 48, 431-442. Agami, C.; Cases, M.; Couty, F. J. Org. Chem. 1994, 59, 7937-7940.
18. 10 Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc. 1985, 107, 3902-3909.