The Staudinger reaction of imines derived from 7-oxanorbornenone: Formation of spiranic oxazinone versus β-lactam rings

Tetrahedron Letters

Volumn 43, Issue 36, 2002, Pages 6405-6408

  Arjona, Odón ^a   Csákÿ, Aurelio G ^a   Murcia, M Carmen ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

7 OXANORBORNENONE; ACETIC ACID DERIVATIVE; BETA LACTAM DERIVATIVE; IMINE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CYCLOADDITION; DIASTEREOISOMER; DRUG SYNTHESIS; STAUDINGER REACTION; STEREOCHEMISTRY;

EID: 0037009717     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01375-8     Document Type: Article

References (32)

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17. For selected, recent reviews, see: (a) Yamamoto, Y.; Asao, N.; Tsukuda, N. In Advances in Asymmetric Synthesis; Hassner, A. H., Ed. Asymmetric Synthesis of β-Aminoacids and β-Lactam Derivatives via Conjugate Addition of Metal Amides. JAI Press: Stamford, CT, 1998; Vol. 3; (b) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675; (c) Doyle, M. P. Pure Appl. Chem. 1998, 70, 1123; (d) Benaglia, M.; Cinquini, M.; Cozzi, F. Eur. J. Org. Chem. 2000, 563; (e) Dirat, O.; Koulovsky, C.; Manduit, M.; Langlois, Y. Pure Appl. Chem. 2000, 72, 1721; (f) Kawabata, T. Rev. Hetereoatom Chem. 2000, 33; (g) For solid phase and combinatorial synthesis, see: Mata, E. G. Curr. Pharm. Des. 1999, 5, 955.
18. For selected, recent reviews, see: (a) Yamamoto, Y.; Asao, N.; Tsukuda, N. In Advances in Asymmetric Synthesis; Hassner, A. H., Ed. Asymmetric Synthesis of β-Aminoacids and β-Lactam Derivatives via Conjugate Addition of Metal Amides. JAI Press: Stamford, CT, 1998; Vol. 3; (b) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675; (c) Doyle, M. P. Pure Appl. Chem. 1998, 70, 1123; (d) Benaglia, M.; Cinquini, M.; Cozzi, F. Eur. J. Org. Chem. 2000, 563; (e) Dirat, O.; Koulovsky, C.; Manduit, M.; Langlois, Y. Pure Appl. Chem. 2000, 72, 1721; (f) Kawabata, T. Rev. Hetereoatom Chem. 2000, 33; (g) For solid phase and combinatorial synthesis, see: Mata, E. G. Curr. Pharm. Des. 1999, 5, 955.
19. For selected, recent reviews, see: (a) Yamamoto, Y.; Asao, N.; Tsukuda, N. In Advances in Asymmetric Synthesis; Hassner, A. H., Ed. Asymmetric Synthesis of β-Aminoacids and β-Lactam Derivatives via Conjugate Addition of Metal Amides. JAI Press: Stamford, CT, 1998; Vol. 3; (b) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675; (c) Doyle, M. P. Pure Appl. Chem. 1998, 70, 1123; (d) Benaglia, M.; Cinquini, M.; Cozzi, F. Eur. J. Org. Chem. 2000, 563; (e) Dirat, O.; Koulovsky, C.; Manduit, M.; Langlois, Y. Pure Appl. Chem. 2000, 72, 1721; (f) Kawabata, T. Rev. Hetereoatom Chem. 2000, 33; (g) For solid phase and combinatorial synthesis, see: Mata, E. G. Curr. Pharm. Des. 1999, 5, 955.
20. For selected, recent reviews, see: (a) Yamamoto, Y.; Asao, N.; Tsukuda, N. In Advances in Asymmetric Synthesis; Hassner, A. H., Ed. Asymmetric Synthesis of β-Aminoacids and β-Lactam Derivatives via Conjugate Addition of Metal Amides. JAI Press: Stamford, CT, 1998; Vol. 3; (b) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675; (c) Doyle, M. P. Pure Appl. Chem. 1998, 70, 1123; (d) Benaglia, M.; Cinquini, M.; Cozzi, F. Eur. J. Org. Chem. 2000, 563; (e) Dirat, O.; Koulovsky, C.; Manduit, M.; Langlois, Y. Pure Appl. Chem. 2000, 72, 1721; (f) Kawabata, T. Rev. Hetereoatom Chem. 2000, 33; (g) For solid phase and combinatorial synthesis, see: Mata, E. G. Curr. Pharm. Des. 1999, 5, 955.
21. . For a selected recent review, see: Palomo C., Aizpurua J.M., Ganboa I., Oiarbide M. Eur. J. Org. Chem. 1999;3223. and references cited therein.
22. Arjona O., Mallo A., Manzano C., Plumet J., Galbis J., Jaime C. J. Chem. Soc., Perkin Trans. 2. 1988;865.
23. Arjona O., Csaky A., Murcia M.C., Plumet J. Helv. Chim. Acta. 84:2001;3667.
24. 7-Oxanorbornene derivatives have been termed naked sugars. For recent reviews, see: (a) Vogel, P.; Cossy, J.; Plumet, J.; Arjona, O. Tetrahedron 1999, 55, 13521; (b) Vogel, P. Curr. Org. Chem. 2000, 4, 455.
25. 7-Oxanorbornene derivatives have been termed naked sugars. For recent reviews, see: (a) Vogel, P.; Cossy, J.; Plumet, J.; Arjona, O. Tetrahedron 1999, 55, 13521; (b) Vogel, P. Curr. Org. Chem. 2000, 4, 455.
26. 2 system exhibited the shielding of one of the hydrogen signals (1H, δ=4.70-4.80 ppm and 1H, δ=3.05-3.10 ppm). This can be accounted for by a shielding effect of the C5-C6 double bond of the oxabicyclic moiety.
27. . Different behaviour of alkyl and alkoxyacetyl chlorides in the Staudinger reaction has been previously reported. See: Georg G.L., He P., Kant J., Wu Z. J. Org. Chem. 58:1993;5571. and references cited therein.
28. exo.
29. exo-Addition is the characteristic reaction way of the carbonyl group of the derivatives of 7-oxanorbornen-5-one. See Ref. 9 .
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31. Arjona O., de la Pradilla R.F., Pérez S., Plumet J. Tetrahedron. 44:1988;1235.
32. . For the participation of this kind of reaction pathway in β-lactam formation under Staudinger reaction conditions see: Arrieta A., Lecea B., Cossío F.P. J. Org. Chem. 63:1998;5869. and references cited therein.