State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences , Lanzhou 73000, China.
University of Chinese Academy of Sciences , Beijing 100049, China.
Org Lett. 2017 Jul 7;19(13):3676-3679. doi: 10.1021/acs.orglett.7b01740. Epub 2017 Jun 21.
A copper-catalyzed asymmetric protoboration of both Z-β-amidoacrylonitriles and ethyl E-β-amidoacrylates using bis(pinacolato)diboron has been developed for the first time. The process tolerates a vast array of substrates, delivering a series of stable functionalized chiral α-amino boronate esters in good yields and enantioselectivities under mild reaction conditions. The current method is also applicable for gram-scale synthesis without erosion of enantioselectivity. This work provides an attractive and complementary approach to synthesizing enantioriched chiral α-amino boronate esters.
首次开发了铜催化的 Z-β-酰胺基丙烯腈和乙基 E-β-酰胺基丙烯酸酯的不对称原硼化反应，使用了双（频哪醇）二硼。该过程耐受大量的底物，在温和的反应条件下以良好的收率和对映选择性得到一系列稳定的官能化手性α-氨基硼酸酯。该方法也适用于克级合成，对映选择性没有降低。这项工作为合成手性丰富的手性α-氨基硼酸酯提供了一种有吸引力和互补的方法。
