Flaget Arthur, Mazet Clément
Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, 1211 Geneva, Switzerland.
Org Lett. 2024 Oct 11;26(40):8542-8547. doi: 10.1021/acs.orglett.4c03170. Epub 2024 Oct 2.
We report Cu-catalyzed enantioselective borylation/oxidation sequences that afford either enantioenriched 1,2- or 1,3-amino alcohols starting from -protected allylamines as a common platform. The approach is based on the mechanistic specificities of catalytic hydroboration and protoboration reactions, which formally install a boron unit and a hydrogen atom at opposite positions of a C═C bond. The nature of the substituents of the carbon-carbon double bond also exerts a determining influence on the regioselectivity of insertion of the catalytically active Cu species. Both protocols are regio- and enantioselective and applicable to a broad range of substrates. Homoallylamines are also competent substrates, providing access to 1,3- and 1,4-amino alcohols.
我们报道了铜催化的对映选择性硼氢化/氧化序列，该序列以受保护的烯丙胺为通用平台，可提供对映体富集的1,2-或1,3-氨基醇。该方法基于催化硼氢化和原硼化反应的机理特异性，这两个反应形式上是在碳-碳双键的相对位置上引入一个硼单元和一个氢原子。碳-碳双键取代基的性质对催化活性铜物种插入的区域选择性也有决定性影响。这两种方法都具有区域选择性和对映选择性，适用于广泛的底物。高烯丙胺也是合适的底物，可用于合成1,3-和1,4-氨基醇。
