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

Ryan Brady, Yelena Khakham, Guillaume Lessene, Jonathan Bayldon Baell

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14 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)656 - 658
Number of pages3
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number3
DOIs
Publication statusPublished - 2011
Externally publishedYes

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