Pyrrolidin-2-ones are important heterocyclic motifs found in natural products and biologically active synthetic molecules. Addition of nucleophiles, incl uding allylsilanes, isonitriles and organometallics , to N - acyliminium ions represents one of the most commonl y used approaches for the formation of substituted pyrrolidin-2-ones. Only few studies on the nucleoph ic addition of organoboronic acids to N -acyliminium ions have been reported. Herein, we disclose our re cent efforts for the synthesis of substituted pyrro lidin- 2-ones through Lewis-acid-mediated Petasis-type rea ctions. By implementing a reductive cyclization reaction, linear L -malic acid derivatives were rapidly converted into cyclic N -acyliminium ions. Under the optimized conditions, entailing the use of HFIP as solvent, both electron-rich and electron-deficient boronic acids were successfully added to a range of cyclic N -acyliminium ions, typically with excellent diastereoselectivity with electron-deficient boroni c acids.
|Journal||ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY|
|Publication status||Published - 2014|
|Event||248th National Fall Meeting of the American Chemical Society - San Francisco, CA, United States|
Duration: 10 Aug 2014 → 14 Aug 2014
|Conference||248th National Fall Meeting of the American Chemical Society|
|City||San Francisco, CA|
|Period||10/08/2014 → 14/08/2014|