253140-65-7Relevant academic research and scientific papers
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.
