GaCl3-promoted ethenylation of silylated β-dicarbonyl compound with silylethyne. Synthesis of ethenylmalonate

Organic Letters

Volumn 3, Issue 5, 2001, Pages 789-790

  Arisawa, Mieko ^a   Akamatsu, Kensuke ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000588488     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015583b     Document Type: Article

References (8)

1. Koppel, G. A.; Kinnick. M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Also see, Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 43, 3757.
2. Koppel, G. A.; Kinnick. M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Also see, Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 43, 3757.
3. Seefelder, M. Liehigs Ann. Chem. 1962, 652, 107.
4. Torgashina, Z. I.; Naumchuk. A. L. J. Gen. Chem., USSR 1956, 26, 3353. The reaction could not be reproduced in our hands. We obtained only diethyl 2,4-di(ethoxycarbonyl)-3-methylpentanedioate, which may be formed by the conjugate addition of malonate to ethylidenemalonate.
5. Adelman, R. L. U.S. 2,550,439: Chem. Abstr. 1951, 45, 8035. The reaction was also not reproducible, and the only product obtained was ethylidenemalonate.
6. Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074.
7. (E)-Stereochemistry of the silyl enol ether is determined by NOE experiment.
8. 4: 214.1205. Found: 214.1198.