Efficient Tandem Process for the Catalytic Deprotection of N-Allyl Amides and Lactams in Aqueous Media: A Novel Application of the Bis(allyl)–Ruthenium(IV) Catalysts [Ru(η3:η2:η3-C12H18)Cl2] and [{Ru(η3:η3-C10H16)(μ-Cl)Cl}2]

✍ Scribed by Victorio Cadierno; José Gimeno; Noel Nebra

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 105 KB
• Volume: 13
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200700477

✦ Synopsis

Abstract

An operationally simple and highly efficient methodology for the removal of the allyl protecting group in amides and lactams has been developed by using the commercially available bis(allyl)–ruthenium(IV) catalysts [Ru(η^3^:η^2^:η^3^‐C~12~H~18~)Cl~2~] (C~12~H~18~=dodeca‐2,6,10‐triene‐1,12‐diyl) and [{Ru(η^3^:η^3^‐C~10~H~16~)(μ‐Cl)Cl}~2~] (C~10~H~16~=2,7‐dimethylocta‐2,6‐diene‐1,8‐diyl). The tandem process, which takes place in aqueous media and proceeds in a one‐pot manner, involves the initial isomerization of the CC bond of the allyl unit and subsequent oxidative cleavage of the resulting enamide.