title: 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.
authors.affiliation: Walter and Eliza Hall Institute of Medical Research, 1G Royal Parade, Parkville, Victoria, 3052, Australia.
authors.forename: Ryan M
authors.initials: RM
authors.lastname: Brady
authors.forename: Yelena
authors.initials: Y
authors.lastname: Khakham
authors.forename: Guillaume
authors.initials: G
authors.lastname: Lessene
authors.forename: Jonathan B
authors.initials: JB
authors.lastname: Baell
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D001554:Benzene / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D014508:Urea / Q000737:chemistry*
chemical_list: D000577:Amides; D014508:Urea; D001554:Benzene