ABSTRACT
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.
Subject(s)
Amides/chemistry , Esters/chemistry , Organosilicon Compounds/chemistry , Phosphinic Acids/chemistry , Phosphopeptides/chemical synthesis , Molecular Structure , Phosphopeptides/chemistry , StereoisomerismABSTRACT
A Lewis acid-catalyzed rearrangement of phosphorimidates allows a direct, high-yielding transformation of azides with commercially available phosphites into secondary phosphoramidates.
ABSTRACT
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.
Subject(s)
Acrylonitrile/chemical synthesis , Amino Acids/chemistry , Combinatorial Chemistry Techniques/methods , Acetates/chemistry , Acrylonitrile/chemistry , Molecular Structure , Solutions/chemistry , StereoisomerismABSTRACT
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.
