80287-81-6Relevant articles and documents
Ring Opening Reactions of Methyl 2-Siloxycyclopropanecarboxylates to Oxoalkanoic Acid Derivatives
Kunkel, Elisabeth,Reichelt, Ingrid,Reissig, Hans-Ulrich
, p. 802 - 819 (2007/10/02)
A great variety of methyl 2-(trialkylsiloxy)cyclopropanecarboxylates C1 - C31 are cleaved under very mild conditions and with excellent yields providing 4-oxoalkanoic esters D1 - D31 which are important synthetic building blocks.Even sensible esters with formyl, vinyl ketone, or trimethylsiloxy functions can be prepared.Corresponding to the regioselective synthesis of C isomeric pairs of D can deliberately be constructed.In the presence of an electrophile alkylating ring opening delivers 4-oxoalkanoates substituted in position 2, however, the degree of alkylation does not exceed 60percent.Several other cleavage variations allow syntheses of other 4-oxoalkanoic acid derivatives in effective one-pot procedures.
Fluoride-Mediated Reactions of Enol Silyl Ethers. Regiospecific Monoalkylation of Ketones
Kuwajima, Isao,Nakamura, Eiichi,Shimizu, Makoto
, p. 1025 - 1030 (2007/10/02)
Treatment of enol silyl ethers with alkyl halides in the presence of benzyltrimethylammonium fluoride and molecular sieves at room temperature gives the corresponding monoalkylated products with high regiospecificity.In most cases no polyalkylated products formed in the reaction.The alkylation reaction is highly chemospecific: esters, epoxides, and even ketones survive the reaction conditions.The reactions of various cyclohexanone derivatives proceed with the preferential axial attack of the electrophile.
