Copper-Catalyzed Regio- and Stereoselective Aminoboration of Alkenylboronates

A copper-catalyzed
aminoboration of alkenyl dan boronates (dan
= 1,8-diamino­naphthyl) with diboron reagents and hydroxylamines
has been developed. The reaction proceeds regio- and stereoselectively
to form the corresponding β-boryl-α-aminoboronic acid
derivatives of potent interest in medicinal chemistry. Additionally,
the ligand-controlled syn/anti diastereoselectivity
switching and preliminary asymmetric catalysis are also described.

本研究开发了一种铜催化的、以烯基dan硼酸酯（dan = 1,8-二氨基萘基）与二硼试剂、羟胺类化合物为底物的氨基硼化反应。该反应以区域和立体选择性的方式进行，可生成在药物化学领域具有重要研究价值的β-硼基-α-氨基硼酸类衍生物。此外，本文还报道了配体调控的顺式/反式非对映选择性切换策略，以及初步的不对称催化研究。