3 years ago

α-Quaternary Mannich Bases through Copper-Catalyzed Amination-Induced 1,2-Rearrangement of Allylic Alcohols

α-Quaternary Mannich Bases through Copper-Catalyzed Amination-Induced 1,2-Rearrangement of Allylic Alcohols
Jian-Guo Sun, Ping Li, Bo Zhang, Wei-Zhi Weng
A novel copper-catalyzed amination-induced 1,2-rearrangement reaction of allylic alcohols has been developed under simple and mild conditions. The commercially available N-fluorobenzenesulfonimide (NFSI) is employed as an amination reagent. In this transformation, not only alkyl, but also aryl substituents can efficiently undergo 1,2-carbon atom migration, thereby providing an efficient and powerful route to prepare a wide range of α-quaternary Mannich bases. The reaction features a broad substrate scope, operational simplicity, and excellent practicality. A novel copper-catalyzed amination-induced 1,2-rearrangement reaction of allylic alcohols has been achieved under simple and mild conditions. This transformation exhibits a broad substrate scope and good functional group tolerance. A variety of Mannich bases containing an α-quaternary center are readily prepared in moderate to excellent yields using the title reaction.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702428

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