Microwave and polymer assisted synthesis of a small library of α,β-unsaturated methyl esters via the Wittig reaction

Letters in Organic Chemistry

Volumn 4, Issue 6, 2007, Pages 384-387

  Collina, Simona ^a   Rossi, D ^a   Urbano, M ^a   Carnevale Baraglia, A ^a   Azzolina, O ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

E:Z isomeric ratio; MAOS; PASPS; Sigma ligands intermediates; Wittig reaction

Indexed keywords

EID: 36148930964     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017807781467650     Document Type: Article

References (19)

1. (a) Matloobi, M.; Kappe, C. O. J. Comb. Chem., 2007, 9, 275;
2. (b) Kremsner, J. M.; Stadler, A.; Kappe, C. O. J. Comb. Chem., 2007, 9, 285;
3. (c) Kou, B.; Zhang, F.; Yang, T. M.; Liu, G. J. Comb. Chem., 2006, 8, 841.
4. (a) Collina, S.; Urbano, M.; Magnani, A.; Loddo, G., Azzolina O. Lett. Org. Chem., 2006, 3, 16;
5. (b) Collina, S.; Loddo, G.; Urbano, M.; Limati, L.; Callegari, A.; Ortuso, F.; Alcaro, S.; Laggner, C.; Langer, T.; Prezzavento O.; Ronsisvalle, G.; Azzolina, O. Bioorg. Med. Chem., 2007, 15, 771.
6. (a) Wittig, G.; Haag, W. Chem. Ber., 1955, 88, 1654;
7. (b) Maryanoff, B. E.; Reitz, A. B.; Chem. Rev., 1989, 89, 863;
8. (c) Beletskaya. I. P.; Cheprakov, A. V. Chem. Rev., 2000, 100, 3009;
9. (d) List, B.; Boehring, A.; Hechavarria Fonseca, M. T.; Job, A.; Torres, R. R. Tetrahedron, 2006, 62, 476.
10. Sabitha, G.; Peddy, M. M.;Srinivas; D.; Yadov, J. S.; Tetrahedron Lett., 1999, 40, 165.
11. Xu, C.; Chen, G.; Fu, C.; Huang, X. Synth. Commun., 1995, 25, 229.
12. Xu; C.; Chen, G.; Huang, X. Org. Prep. Proced. Int., 1995, 27, 559.
13. Vu, C.; Xu, C.; G.; Huang, Z. Org. Prep. Proced. Int., 1997, 29, 587.
14. Yu, X.; Huang, X. Synlett., 2002, 1895.
15. Frattitti, S.; Quai, M.; Cereda, E. Tetrahedron Lett., 2001, 42, 6827.
16. Westman, J. Org. Lett., 2001, 3, 3745.
17. 3CN using stabilized phosphorous ylide (1 equiv) under microwave irradiation at 150°C, 100 watt for 10 minutes. All compounds were purified using flash chromatography on Silica ICN BIOMEDICAL (60Å); eluent: n-hexane/ethylacetate (6/4).
18. General praedure for MAOS and PASPS protocol: the reactions were conducted on 0.5 mmol scale in 3 mL MeOH using methyl bromoacetate (4 equiv), AcONa4 (4 equiv) and TPP potymer-bound (2 equiv) under microwave irradiation at 150°C, 100 watt for 10 minutes. Reaction work-up: the sample was dissolved in diethyl ether, washed sequentially with water and brine, dried over anhydrous sodium sulphate and evaporated to dryness.
19. 4: C, 66.09; H, 6.93. Found: C, 66.17; H, 6.65.