Polymer-supported electron-rich diene for hetero Diels-Alder reactions

Tetrahedron Letters

Volumn 44, Issue 18, 2003, Pages 3645-3647

  Pierres, Camille ^a   George, Pascal ^b   Van Hijfte, Luc ^b,c   Ducep, Jean Bernard ^b   Hibert, Marcel ^a   Mann, André ^a  

^a Laboratoire de Pharmacochimie   (France)

^b SANOFI   (France)

^c Johnson Johnson Pharmaceutical R   (France)

Author keywords

5,6 dihydropyrones; Hetero Diels Alder; Solid supported reagent

Indexed keywords

ALDEHYDE; ALKADIENE; ALKENE DERIVATIVE; KETONE; POLYMER; RESIN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIELS ALDER REACTION; ELECTRON;

BETULACEAE;

EID: 0037471463     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00712-3     Document Type: Article

References (17)

1. For excellent reviews on the Diels-Alder reaction, see: Corey, E. J. Angew. Chem. 2002, 41, 1650-1667, and Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassililogiannakis, G. Angew. Chem. 2002, 41, 1668-1698.
2. For excellent reviews on the Diels-Alder reaction, see: Corey, E. J. Angew. Chem. 2002, 41, 1650-1667, and Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassililogiannakis, G. Angew. Chem. 2002, 41, 1668-1698.
3. For a review on solid supported Diels-Alder reactions, see: Kanhaluona J.Y. Tetrahedron. 57:2001;7053.
4. Klohs M.W., Keller F., Williams R.E., Tockes M.I., Cronheim G.E. J. Med. Chem. 1:1959;95-103.
5. Boyer F.E., Vara Prasad J.V.N., Domagala J.M. J. Med. Chem. 43:2000;843-858.
6. Brassard P., Savard J. Tetrahedron Let. 20:1979;4911-4914.
7. Midland M.M., Koops R.W. J. Org. Chem. 55:1990;5058-5065.
8. Waldmann H., Braun M., Draeger M. Tetrahedron: Asymmetry. 2:1991;1231-1246.
9. Colvin E. Silicon Reagents in Organic Synthesis. 1988;99 Academic Press.
10. Coleman R.S., Grant E.B. J. Am. Chem. 117:1995;10889-10904.
11. Takemura S., Hirayama A., Tokunaga J., Kawamura F., Inagaki K., Hashimoto K., Nakata M. Tetrahedron Lett. 40:1999;7501-7505.
12. Tietze L.F., Steinmetz A. Angew. Chem. 35:1996;651-652.
13. The Merrifield support was purchased from Novabiochem 1% DVB, 200-400 mesh, 1-1.5 mmol/g. The loading on resin B was determined by the Fmoc technique and was 0.65 mmol/g.
14. 4) δ 158.4, 79.2, 76.9, 72.2, 66.1, 64.6, 53.4, 40.2, 29.3, 25.7, 17.9, -3.9.
15. 3) δ 171.1, 166.3, 134.3, 132.7, 129.3, 128.6, 126.3, 126.1, 90.1, 78.3, 55.9, 40.1, 36.3, 32.8, 25.9.
16. Borsche W., Blount B.K. Ber. Dtsch. Chem. Ges. 66:1933;803-806.
17. For an excellent review on supported reagents see: Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., Taylor S.J. J. Chem. Soc., Perkin 1. 2000;3815-4195.