Synthesis of Substituted 1,2-Dihydropyridines from Propargyl Vinyl Ethers and Allenic Vinyl Ethers by Gold-Catalyzed Claisen Rearrangement and 6π-Aza-electrocyclization

✍ Scribed by Hao Wei; Yao Wang; Bin Yue; Peng-Fei Xu

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 175 KB
• Volume: 352
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.201000292

✦ Synopsis

Abstract

An efficient synthetic method was developed for the construction of substituted 1,2‐dihydropyridines by gold‐catalyzed tandem reactions. The key intermediates 2,4‐dienals were generated from propargyl vinyl ethers or allenic vinyl ethers with gold catalysts. These two reactions involved the process of gold‐catalyzed [3,3]‐sigmatropic rearrangement/isomerization/amine condensation/6π‐aza‐electrocyclization.