A carbonyl ylide approach to substituted furans

Synlett

Volumn , Issue 5, 2001, Pages 646-648

  Johnson, Tim ^a   Cheshire, David R ^a   Stocks, Michael J ^a   Thurston, Vicky T ^b  

^a ASTRAZENECA   (United Kingdom)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

Carbonyl ylide; Diazo compounds; Furans; Ring closure

Indexed keywords

ALDEHYDE; ALKENE; ALKYNE; CARBONYL DERIVATIVE; CARBONYL YLIDE DERIVATIVE; FURAN DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; CHEMICAL INTERACTION; HEATING; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0035038378     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2001-13355     Document Type: Article

References (17)

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2. For some examples of intermolecular carbonyl ylide generation see: Hamaguchi, M.; Matsubara, H.; Nagai, T. Tetrahedron Lett. 2000, 41, 1457. Doyle, M. P.; Forbes, D. C.; Xavier, K. R. Russ. Chem. Bull. 1998, 47, 932. Ibata, T.; Liu, M. T. H.; Toyoda, J. Tetrahedron Lett. 1986, 27, 4383.
3. For some examples of intermolecular carbonyl ylide generation see: Hamaguchi, M.; Matsubara, H.; Nagai, T. Tetrahedron Lett. 2000, 41, 1457. Doyle, M. P.; Forbes, D. C.; Xavier, K. R. Russ. Chem. Bull. 1998, 47, 932. Ibata, T.; Liu, M. T. H.; Toyoda, J. Tetrahedron Lett. 1986, 27, 4383.
4. For some examples of intermolecular carbonyl ylide generation see: Hamaguchi, M.; Matsubara, H.; Nagai, T. Tetrahedron Lett. 2000, 41, 1457. Doyle, M. P.; Forbes, D. C.; Xavier, K. R. Russ. Chem. Bull. 1998, 47, 932. Ibata, T.; Liu, M. T. H.; Toyoda, J. Tetrahedron Lett. 1986, 27, 4383.
5. Doyle, K. J.; Moody, C. J. Tetrahedron 1994, 50, 3761.
6. General experimental procedure for the synthesis of furans 6. A mixture of aldehyde 4 (0.5 mmol), dimethylacetylene dicarboxylate (0.5 mmol), methyldiazo(benzenesulphonyl) acetate 1 (0.5 mmol), rhodium octanoate dimer (0.025 mmol) and 1,2-dichloroethane (0.5 mL) was stirred at room temperature for 1 hour. Triethylamine (0.5 mmol) and 1,2-dichloroethane (0.5 mL) were added and the solution was heated at 65 °C for 2 hours. Column chromatography (silica, eluent iso-hexane/ether 95:5) was used to obtain pure products 6.
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14. Formula represented
15. General experimental procedure for the synthesis of annulated furans 10 and tetrahydrofurans 12. To a mixture of aldehyde 9 or 11 (0.5 mmol), methyldiazo(benzenesulphonyl) acetate 1 (0.5 mmol) and 1,2-dichloroethane (0.1 mL) at 65 °C was added a slurry of rhodium octanoate dimer (0.025 mmol) in 1,2-dichloroethane (0.3 mL). The reaction mixture was heated at 65 °C for a further 0.75 hour. Column chromatography (silica, eluent iso-hexane/ether 95:5) was used to obtain pure products 10 or 12.
16. Spino, C.; Barriault, N. J. Org. Chem. 1999, 64, 5292.
17. 3: C, 74.36; H, 5.82. Found: C, 74.16; H, 6.26.