Benzoylureas as removable cis amide inducers: Synthesis of cyclic amides via ring closing metathesis (RCM)

Abstract

Rapid and high yielding synthesis of medium ring lactams was made possible through the use of a benzoylurea auxiliary that serves to stabilize a cisoid amide conformation, facilitating cyclization. The auxiliary is released after activation under the mild conditions required to deprotect a primary amine, such as acidolysis of a Boc group in the examples given here. This methodology is a promising tool for the synthesis of medium ring lactams, macrocyclic natural products and peptides. © 2011 The Royal Society of Chemistry.