中国科学院上海有机化学研究所施世良团队报道了镍/N-杂环碳催化醛与有机硼的对映选择性烷基化。相关研究成果发表在2024年5月11日出版的国际知名学术期刊《中国化学》。

过渡金属催化的醛不对称烷基化是合成手性仲醇的一种直接策略。然而，使用有机硼作为偶联试剂的有效方法是罕见的。

该文中，研究人员报道了一种使用容易获得的烷基硼作为亲核试剂的，高度对映选择性的镍催化的醛烷基化反应。以市售醛为原料，以高产率制备了多种手性仲醇。优异的对映选择性和化学选择性的关键是使用体积庞大的C2对称手性NHC配体。该方案具有良好的对映体控制、温和的条件和良好的官能团兼容性。

附：英文原文

Title: Enantioselective Alkylation of Aldehydes with Organoborons Enabled by Nickel/N-Heterocyclic Carbene Catalysis†

Author: Song-Yang Liu, Zi-Chao Wang, Shi-Liang Shi

Issue&Volume: 2024-05-11

Abstract: Transition-metal-catalyzed asymmetric alkylation of aldehydes represents a straightforward strategy for the synthesis of chiral secondary alcohols. However, efficient methods using organoborons as coupling reagents are rare. Herein, we report a highly enantioselective nickel-catalyzed alkylation reaction of aldehydes, using readily available alkylborons as nucleophiles. A wide variety of chiral secondary alcohols were prepared from commercially available aldehydes with high yields. The key to the excellent enantioselectivity and chemoselectivity was the employment of a bulky C2-symmetric chiral NHC ligand. This protocol features excellent enantiocontrol, mild conditions, and good functional group compatibility.

DOI: 10.1002/cjoc.202400288

Source: https://onlinelibrary.wiley.com/doi/full/10.1002/cjoc.202400288