Switching stereocontrol in the high pressure-induced hetero-Diels-Alder reaction

Chemical Communications

Volumn , Issue 13, 2000, Pages 1191-1192

  Al Badri, Hashim ^a   Collignon, Noël ^b   Maddaluno, Jacques ^a   Masson, Serge ^c  

^a UNIVERSITÉ DE ROUEN   (France)

^b CNRS   (France)

^c UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; HETERODUPLEX;

ARTICLE; CHEMICAL REACTION; ISOMERISM; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0034617268     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b003060k     Document Type: Article

References (17)

1. Review: G. Jenner, Tetrahedron, 1997, 53, 2669:
2. for recent important results, see: (a) S. Hillers and O. Reiser, Chem. Commun., 1996, 2197;
3. (b) F.-G. Klärner and V. Breitkopf, Eur. J. Org. Chem., 1999, 2757;
4. (c) G. J. Kuster and H. W. Scheeren, Tetrahedron Lett., 2000, 41, 515.
5. L. F. Tietze, M. Henrich, A. Niklaus and M. Buback, Chem. Eur. J., 1999, 5, 297 and references therein.
6. H. Al-Badri, J. Maddaluno, S. Masson and N. Collignon, J. Chem. Soc., Perkin Trans. 1, 1999, 2225.
7. H. Al-Badri, N. Collignon, J. Maddaluno and S. Masson, Tetrahedron, 2000, 56, 3909.
8. We prepared 1d by condensing methyl acetoacetate with benzaldehyde bis(morpholino)aminal (following the procedure described in ref. 3), instead of benzaldehyde used by: C. A. Kingsbury, D. Draney, A. Sopchik, W. Rissler and D. Durham, J. Org. Chem., 1976, 41, 3863.
9. The separation of the isomers was achieved by using a Waters HPLC chromatograph, a Nova Pack (L = 10 cm, Φ = 0.8 cm) silica gel column and heptane/AcOEt (97:3) as eluent.
10. An example of light-promoted (E)/(Z)-heterodiene isomerization preceding the cycloaddition has been reported by: L. F. Tietze, T. Brumby, M. Pretor and G. Remberg, J. Org. Chem., 1988, 53, 810.
11. (E)-1a was configurationally stable in the presence of pyridine, at 20 °C and atmospheric pressure for several days.
12. High pressure-induced hetero-Michael additions of primary amines have been described in the literature [see for example: (a) J. d'Angelo and J. Maddaluno, J. Am. Chem. Soc., 1986, 108, 8112;
13. (b) F. Dumas, B. Mezrhab, J. d'Angelo, C. Riche and A. Chiaroni, J. Org. Chem., 1996, 61, 2293], and are currently under study in our laboratories (A. Y. Rulev, J. Maddaluno, G. Plé, J. C. Plaquevent and L. Duhamel, J. Chem. Soc., Perkin Trans. 1, 1998, 1397, and work in preparation).
14. (b) F. Dumas, B. Mezrhab, J. d'Angelo, C. Riche and A. Chiaroni, J. Org. Chem., 1996, 61, 2293], and are currently under study in our laboratories (A. Y. Rulev, J. Maddaluno, G. Plé, J. C. Plaquevent and L. Duhamel, J. Chem. Soc., Perkin Trans. 1, 1998, 1397, and work in preparation).
15. In each case, we verified, first, that the starting diene was configurationally stable at 11 kbar in the absence of pyridine, and secondly that the obtained cycloadduct mixture did not isomerize, at 11 kbar, in the presence of pyridine.
16. The postulated addition of the nucleophilic pyridine to the heterodiene is to be considered in relation to the first step of the Baylis-Hillman reaction, which is known to be very sensitive to pressure; see for instance: A. Gilbert, T. W. Heritage and N. S. Isaacs, Tetrahedron: Asymmetry, 1991, 2, 969; I. E. Markó, P. R. Giles and N. J. Hindley, Tetrahedron, 1997, 53, 1015.
17. The postulated addition of the nucleophilic pyridine to the heterodiene is to be considered in relation to the first step of the Baylis-Hillman reaction, which is known to be very sensitive to pressure; see for instance: A. Gilbert, T. W. Heritage and N. S. Isaacs, Tetrahedron: Asymmetry, 1991, 2, 969; I. E. Markó, P. R. Giles and N. J. Hindley, Tetrahedron, 1997, 53, 1015.