Synthesis of phosphonamidate peptides by Staudinger reactions of silylated phosphinic acids and esters.

The Staudinger reaction of unprotected azido-peptides with silylated phosphinic acids and esters on the solid support offers a straightforward acid-free entry to different phosphonamidate peptide esters or acids under mild conditions in high purity and yield.

Synthesis of N,N-disubstituted phosphoramidates via a Lewis acid-catalyzed phosphorimidate rearrangement.

A Lewis acid-catalyzed rearrangement of phosphorimidates allows a direct, high-yielding transformation of azides with commercially available phosphites into secondary phosphoramidates.

Parallel solution-phase synthesis of acrylonitrile scaffolds carrying L-alpha-amino acidic or D-glycosyl residues.

A practical and straightforward protocol for the preparation of a solution-phase library of acrylonitrile scaffolds is reported. Target compounds were obtained in high yield, stereoselectivity, and purity by two simple and practical steps from cyanoacetic acid. Moreover, our study proposes a synthetic approach starting from the constructed library to obtain three-membered heterocycles.

First asymmetric synthesis of (-)-lintetralin via intramolecular Friedel-Crafts-type cyclization.

The asymmetric synthesis of an aryltetralin lignan, (-)-lintetralin, was achieved with an overall yield of 29% with seven steps. Key features of the synthesis are an asymmetric Strecker reaction, a diastereoselective Michael addition of the lithiated amino nitrile product to 5H-furan-2-one, and an intramolecular carbocationic cyclization to provide the desired ring skeleton with the correct configuration.