Reactions of 1-acylamino-1-(trimethylsiloxy)alkanes: versatile precursors to acylimines

Abstract

1-Acylamino-1-(trimethylsiloxy)alkanes react with carbon and heteroatom nucleophiles to give the corresponding 1-substituted-1-acylaminoalkanes. The 1-acylamino-1-(trimethylsiloxy)alkanes can also give rise to enamides, and by this route the mild antibiotic tuberin, and the isomeric (Z)-tuberin have been prepared. A further example of their reactions is illustrated with the acid-catalysed intramolecular cyclisation onto a carbon–carbon double bond. These transformations show that 1-acylamino-1-(trimethylsiloxy)alkanes are versatile precursors to synthetically useful acylimines.