81255-63-2Relevant academic research and scientific papers
α-Quaternary Mannich Bases through Copper-Catalyzed Amination-Induced 1,2-Rearrangement of Allylic Alcohols
Weng, Wei-Zhi,Sun, Jian-Guo,Li, Ping,Zhang, Bo
supporting information, p. 9752 - 9755 (2017/07/25)
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.
Copper-catalyzed cyanomethylation of allylic alcohols with concomitant 1,2-aryl migration: Efficient synthesis of functionalized ketones containing an α-quaternary center
Bunescu, Ala,WangDr, Qian,Zhu, Jieping
supporting information, p. 3132 - 3135 (2015/04/14)
A copper-catalyzed alkylation of allylic alcohols by alkyl nitriles with concomitant 1,2-aryl migration was developed. Formation of the alkyl nitrile radical was followed by its intermolecular addition to alkenes and the migration of a vicinal aryl group with the concomitant generation of a carbonyl functionality to complete the domino sequence. Mechanistic studies suggested that 1,2-aryl migration proceeded through a radical pathway (neophyl rearrangement). The protocol provided an efficient route to functionalized ketones containing an α-quaternary center.
