Novel and effective synthesis of 2-acyloxy-3-keto esters

Synthesis

Volumn , Issue 11, 2006, Pages 1767-1770

  Komiyama, Takuzo ^a   Takaguchi, Yutaka ^a   Tsuboi, Sadao ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Epoxides; Ketones; Rearrangements; Ring opening; Tandem reactions

Indexed keywords

ACETONITRILE; CARBOXYLATION; ESTERIFICATION; KETONES; REACTION KINETICS;

EPOXIDES; REARRANGEMENTS; RING-OPENING; TANDEM REACTIONS;

ESTERS;

ACETONITRILE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; ETHYL 2 ACETOXY 3 OXO 4 PHENYLBUTANOATE; ETHYL 2 ACETOXY 3 OXOHEPTANOATE; ETHYL 2 ACETOXY 3 OXOHEXANOATE; ETHYL 2 ACETOXY 3 OXONONANOATE; ETHYL 2 ACETOXY 3 OXOOCTANOATE; ETHYL 2 ACETOXY 4 METHYL 3 OXOPENTANOATE; ETHYL 2 ACETOXY 5 METHYL 3 OXOHEXANOATE; METHYL 2 ACETOXY 3 OXOHEXANOATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; DARZENS REACTION; PROTON TRANSPORT; SYNTHESIS;

EID: 33745141588     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926468     Document Type: Article

References (15)

1. (a) Takeda, A.; Amano, E.; Tsuboi, S. Bull. Chem. Soc. Jpn. 1977, 50, 2191.
2. (b) Hecker, S. J.; Werner, K. M. J. Org. Chem. 1993, 58, 1762.
3. (c) Chen, D.; Sprules, T. J.; Lavallee, J.-F. Bioorg. Med. Chem. Lett. 1995, 5, 759.
4. (d) Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J.; Pflum, D. A.; Petsch, D. T. J. Am. Chem. Soc. 1997, 119, 9641.
5. (a) Henecka, H. Chem. Ber. 1948, 81, 179.
6. (b) Zhao, M.-X.; Wang, M.-X.; Yu, C.-Y.; Huang, Z.-T.; Fleet, G. W. J. J. Org. Chem. 2004, 69, 997.
7. (c) Scheid, G.; Kuit, W.; Ruijter, E.; Orru, R. V. A.; Henke, E.; Bornscheuer, U.; Wessjohann, L. A. Eur. J. Org. Chem. 2004, 1063.
8. Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. J. Am. Chem. Soc. 2005, 127, 12244.
9. Grison, C.; Coutrot, F.; Comoy, C.; Lemilbeau, C.; Coutrot, P. Tetrahedron Lett. 2000, 41, 6571.
10. (a) Tsuboi, S.; Furutani, H.; Takeda, A. Synthesis 1987, 292.
11. (b) Coutrot, P.; Grison, C.; Tabyaoui, M.; Czernecki, S.; Valery, J. M. J. Chem. Soc., Chem. Commun. 1988, 1515.
12. Janecki, T.; Bodalski, R. Heteroat. Chem. 2000, 11, 115.
13. Amos, J.; Castro, B.; Selve, C. Bull. Soc. Chim. Fr. 1993, 130, 683.
14. (a) Takeda, A.; Wada, S.; Fujii, M.; Tanaka, H. Bull. Chem. Soc. Jpn. 1970, 43, 2997.
15. (b) Tsuboi, S.; Furutani, H.; Takeda, A.; Kawazoe, K.; Sato, S. Bull. Chem. Soc. Jpn. 1987, 60, 2475.