65946-56-7Relevant academic research and scientific papers
A convenient method for the lewis base-catalyzed synthesis of α,β-unsaturated carboxylic esters using trimethylsilylketene ethyl trimethylsilyl acetal and carbonyl compounds
Michida, Makoto,Mukaiyama, Teruaki
, p. 704 - 705 (2008/12/21)
A highly useful method for the synthesis of α,β-unsaturated carboxylic esters from various carbonyl compounds that uses trimethylsilylbetene ethyl trimethylsilyl acetal in the presence of a Lewis base catalyst such as acetate salts was established. This procedure gives the corresponding esters in high yields with excellent E stereoselectivity under mild conditions. Copyright
Formation of 1-ethenylcyclopropanols involving Kulinkovich cyclopropanation and Peterson olefination of α-trimethylsilylesters
Hazelard, Damien,Ollivier, Jean,Paugam, Renée,Salaün, Jacques
, p. 1155 - 1159 (2007/10/03)
Mercuric iodide catalyzed condensation of bis-silylketene acetals with benzaldehyde provided a 1:1 erythro and threo mixture of α-trimethylsilylesters. Only the threo adducts underwent titanium(IV)-mediated cyclopropanation and acid induced Peterson olefination to provide (Z)-1-ethenylcyclopropanols of considerable synthetic potential.
Michael-Type Addition of O-Ethyl-C,O-bis(trimethylsilyl)ketene Acetal and its Application to the Synthesis of α-Ylidene-δ-lactones
Matsuda, Isamu
, p. 307 - 316 (2007/10/02)
O-Ethyl-C,O-bis(trimethylsilyl)ketene acetal behaves as an active C2 chainlenghtening unit when with α,β-unsaturated ketones yielding δ-keto-α-trimethylsilylesters with the aid of titanium tetrachloride.The products readily form α-ylidene-δ-lactone derivatives after selective reduction of the ketone carbonyl and subsequent Peterson type olefination.
Reactions of Trialkylsilyl Trifluoromethanesulfonates, II. - Synthesis of O-Alkyl-O-(trialkylsilyl)ketene Acetals and 2-(Trialkylsilyl)carboxylates
Emde, Herbert,Simchen, Gerhard
, p. 816 - 834 (2007/10/02)
Alkyl carboxylates 2 are silylated by trialkylsilyl triflates 1 in the presence of triethylamine (3) to yield ketene acetals 4.In reactions of the esters 6 mixtures of ketene acetals 7 and at the α-carbon silylated esters 8 are obtained.Ethanoic acid esters and lactones are doubly silylated to give the products 11, 12, and 15, respectively.Under suitable conditions silylation of the esters 10 gives rise to the 2-trimethylsilylethanoic acid esters 13.The thermodynamically more stable products are obtained.Product distributions depend on the structure of the esters and the silylating agents 1.
