Studies on the α-acetylation of δ-valerolactone and ε-caprolactone

Tetrahedron

Volumn 59, Issue 21, 2003, Pages 3769-3778

  Christoffers, Jens ^a   Oertling, Heiko ^a   Fischer, Peter ^a   Frey, Wolfgang ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Acylation; Lactones; Macrocycles; Metathesis; dicarbonyl compounds

Indexed keywords

1,1 BIS(OXEPAN 2 ON 1 YL)ETHANOL; 2 TRIMETHYLSILYLOXY 4,5,6,7 TETRAHYDROOXEPIN; 3,10 DIACETYL 2,9 DIOXO 1,8 DIOXYACYCLOTETRADECANE; 6 TRIMETHYLSILYLOXY 3,4 DIHYDRO 2H PYRAN; ACETIC ANHYDRIDE; ALCOHOL DERIVATIVE; ALKENE; ALPHA ACETYL DELTA VALEROLACTONE; CAPROLACTONE; DIMER; ESTER; ETHER DERIVATIVE; LACTONE DERIVATIVE; LEWIS ACID; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ALKYLATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; MATERIAL STATE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; RING CLOSING METATHESIS; SYNTHESIS; TRANSESTERIFICATION; X RAY CRYSTALLOGRAPHY;

EID: 0038737177     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00511-8     Document Type: Article

References (31)

1. Christoffers J., Mann A. Angew. Chem. 112:2000;2871-2874. Angew. Chem. Int. Ed. 2000, 39, 2752-2754.
2. (a) Korte F., Machleidt H. Chem. Ber. 90:1957;2137-2149
3. (b) Korte F., Büchel K.-H., Scharf D., Zschocke A. Chem. Ber. 92:1959;884-894.
4. Raulins N.R., Berdahl D.R., Bury T.G. J. Org. Chem. 45:1980;920-922.
5. Hintzer K., Weber R., Schurig V. Tetrahedron Lett. 22:1981;55-58.
6. Christoffers J., Oertling H., Fischer P., Frey W. Synlett. 2002;957-961.
7. Christoffers J., Önal N. Eur. J. Org. Chem. 2000;1633-1635.
8. Lermer L., Neeland E.G., Ounsworth J.P., Sims R.J., Tischler S.A., Weiler L. Can. J. Chem. 70:1992;1427-1445.
9. Djakovitch L., Eames J., Fox D.J., Sansbury F.H., Warren S. J. Chem. Soc., Perkin Trans. 1. 1999;2771-2782.
10. Review: Schuster M., Blechert S. Chemie Unserer Zeit. 35:2001;24-29.
11. Review: Trnka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18-29.
12. Review: Fürstner A. Angew. Chem. 112:2000;3140-3172. Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
13. Review: Blechert S. Pure Appl. Chem. 71:1999;1393-1399.
14. Review: Grubbs R.H., Chang S. Tetrahedron. 54:1998;4413-4450.
15. Review: Armstrong S.K. J. Chem. Soc., Perkin Trans. 1. 1998;371-388.
16. Review: Schuster M., Blechert S. Angew. Chem. 109:1997;2124-2144. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
17. Recent example for macrolactones: Lee C.W., Grubbs R.H. J. Org. Chem. 66:2001;7155-7158.
18. Nakamura K., Miyai T., Nagar A., Oka S., Ohno A. Bull. Chem. Soc. Jpn. 62:1989;1179-1187.
19. Ralls J.W., Lundin R.E., Bailey G.F. J. Org. Chem. 28:1963;3521-3526.
20. Scholl M., Ding S., Lee C.W., Grubbs R.H. Org. Lett. 1:1999;953-956.
21. Herrmann W.A., Kohl F.J., Schwarz J. Herrmann W.A. Transition Metals Part 3. Transition Metals Part 3. Vol. 9:2000;106-112 Thieme, Stuttgart.
22. Gessler S., Randl S., Blechert S. Tetrahedron Lett. 41:2000;9973-9976.
23. Fischer P., Gräf R., Stezowski J.J., Weidlein J. J. Am. Chem. Soc. 99:1977;6131-6132.
24. Fürstner A., Thiel O.R., Ackermann L. Org. Lett. 3:2001;449-451.
25. Rubottom G.M., Gruber J.M., Marrero R., Juve H.D., Kim C.W. J. Org. Chem. 48:1983;4940-4944.
26. Mukai C., Suzuki K., Nagami K., Hanaoka M. J. Chem. Soc., Perkin Trans. 1. 1992;141-145.
27. Mukai C., Mihira A., Hanaoka M. Chem. Pharm. Bull. 39:1991;2863-2866.
28. Mukai C., Suzuki K., Hanaoka M. Chem. Pharm. Bull. 38:1990;567-569.
29. Dess D.B., Martin J.C. J. Am. Chem. Soc. 113:1991;7277-7287.
30. Wallace I.H.M., Chan T.H. Tetrahedron. 39:1983;847-853.
31. Yoshida Y., Matsumoto N., Hamasaki R., Tanabe Y. Tetrahedron Lett. 40:1999;4227-4230.