Jin Shengfei, Dang Hang T, Haug Graham C, Nguyen Viet D, Arman Hadi D, Larionov Oleg V
Department of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA
Chem Sci. 2020 Jul 1;11(34):9101-9108. doi: 10.1039/d0sc03118f.
Construction of C-C bonds at the α-carbon is a challenging but synthetically indispensable approach to α-branched carbonyl motifs that are widely represented among drugs, natural products, and synthetic intermediates. Here, we describe a simple approach to generation of boron enolates in the absence of strong bases that allows for introduction of both α-alkyl and α-aryl groups in a reaction of readily accessible 1,2-dicarbonyls and organoboranes. Obviation of unselective, strongly basic and nucleophilic reagents permits carrying out the reaction in the presence of electrophiles that intercept the intermediate boron enolates, resulting in two new α-C-C bonds in a tricomponent process.
在α-碳上构建碳-碳键是一种具有挑战性但在合成中不可或缺的方法，用于构建α-支链羰基结构单元，这些结构单元在药物、天然产物和合成中间体中广泛存在。在此，我们描述了一种在无强碱条件下生成硼烯醇盐的简单方法，该方法能够在易于获得的1,2-二羰基化合物与有机硼烷的反应中引入α-烷基和α-芳基。避免使用非选择性、强碱性和亲核性试剂，使得该反应能够在亲电试剂存在的情况下进行，亲电试剂会捕获中间体硼烯醇盐，从而在一个三组分过程中形成两个新的α-碳-碳键。
