Chen Weijie, Kang YoungKu, Wilde Richard G, Seidel Daniel
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://seidel-group.com/
Angew Chem Int Ed Engl. 2014 May 12;53(20):5179-82. doi: 10.1002/anie.201311165. Epub 2014 Apr 1.
In contrast to the continuously growing number of methods that allow for the efficient α-functionalization of amines, few strategies exist that enable the direct functionalization of amines in the β-position. A general redox-neutral strategy is outlined for amine β-functionalization and α,β-difunctionalization that utilizes enamines generated in situ. This concept is demonstrated in the context of preparing polycyclic N,O-acetals from simple 1-(aminomethyl)-β-naphthols and 2-(aminomethyl)-phenols.
与能够实现胺高效α-官能化的方法数量不断增加形成对比的是,能够实现胺β-位直接官能化的策略很少。本文概述了一种通用的氧化还原中性策略,用于胺的β-官能化和α,β-双官能化,该策略利用原位生成的烯胺。在从简单的1-(氨基甲基)-β-萘酚和2-(氨基甲基)-苯酚制备多环N,O-缩醛的背景下展示了这一概念。