Aminosilanes in Organic Synthesis. Addition of Organocopper Reagents on γ-Bis(trimethylsilyl)amino-α-Acetylenic Amides, Esters and Ketones. Stereochemistry und Some Synthetic Uses

Article abstract of DOI:10.1016/S0040-4020(01)81289-8

The stereochemical outcome of the carbocupration of γ-bis(trimethylsilyl)amino-α-acetylenic amide, esters and ketone was studied.A judicious choice of substrate, reagent and(or) reaction conditions allows to perform highly stereoselective cis or trans addition.The intermediate vinylic copper adducts, with (E) or (Z) configuration, react with electrophilic reagents to provide short routes to substituted pyrrolinones and pyrroles.Keywords: Silylamines, propargylamines, organocopper regaents, stereochemistry, nitrogen heterocycles.