Qi Qingqing, Yang Xuena, Fu Xiaoping, Xu Shiqing, Negishi Ei-Ichi
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN, 47907, USA.
Angew Chem Int Ed Engl. 2018 Nov 12;57(46):15138-15142. doi: 10.1002/anie.201809389. Epub 2018 Oct 19.
Herein we report a highly efficient and enantiospecific borylation method to synthesize a wide range of enantiopure (>99 % ee) α-amino tertiary boronic esters. The configurationally stable α-N-Boc substituted tertiary organolithium species and pinacolborane (HBpin) underwent enantiospecific borylation at -78 °C with the formation of a new stereogenic C-B bond. This reaction has a broad scope, enabling the synthesis of various α-amino tertiary boronic esters in excellent yields and, importantly, with universally excellent enantiospecificity (>99 % es) and complete retention of configuration.
在此，我们报道了一种高效且对映体特异性的硼化方法，用于合成多种对映体纯的（>99% ee）α-氨基叔硼酸酯。构型稳定的α-N-Boc取代的叔有机锂物种与频哪醇硼烷（HBpin）在-78°C下进行对映体特异性硼化反应，形成新的手性C-B键。该反应适用范围广泛，能够以优异的产率合成各种α-氨基叔硼酸酯，重要的是，具有普遍优异的对映体特异性（>99% es）和构型完全保持。
