Hydrolytic Deallylation of N-Allyl Amides Catalyzed by PdII Complexes

✍ Scribed by Naoya Ohmura; Asami Nakamura; Akiyuki Hamasaki; Makoto Tokunaga

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 149 KB
• Volume: 2008
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200800771

✦ Synopsis

Abstract

Hydrolytic deallylation of N‐allyl amides to give amides and propanal can be achieved with Pd^II^ catalysts. The optimized catalyst consists of Pd(OCOCF~3~)~2~ and 1,3‐bis(diphenylphosphanyl)propane (DPPP). Several kinds of open‐chain N‐allyl amides and N‐allyl lactams undergo hydrolytic deallylation to give the corresponding amides and lactams in good to high yield. A mechanism which includes isomerization to enamides and subsequent hydrolysis is proposed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)