Copper-Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β-and γ-Aminoalkyl)boronic Esters
作者:Nina Ursinyova、Robin B. Bedford、Timothy Gallagher
DOI:10.1002/ejoc.201501492
日期:2016.2
Abstract Cyclic sulfamidates undergo borylation under copper‐catalyzed conditions using B2pin2 to give enantiomerically (and diasteromerically) defined (aminoalkyl)boronic esters. External iodide is essential, but the intermediacy of simple alkyl iodides has been excluded; N‐sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement
摘要 环状磺酰胺在
铜催化条件下使用 B2pin2 进行
硼酸化,得到对映异构(和非对映异构)定义的(
氨基烷基)
硼酸酯。外部
碘化物是必不可少的,但简单的烷基
碘化物已被排除在外;N-
硫酸化中间体是
硼酸化序列中的关键。基于立体
化学研究和捕获实验,在这些
铜催化条件下碳中心自由基的参与似乎是可能的。