Ligand-Promoted, Boron-Mediated Chemoselective Carboxylic Acid Aldol Reaction
Ligand-Promoted, Boron-Mediated Chemoselective Carboxylic Acid Aldol Reaction
复制标题
配体促进、硼介导的化学选择性羧酸羟醛反应
DOI：
10.1021/acs.orglett.6b00914
复制
发表时间：
2016
期刊：
影响因子：
5.2
通讯作者：
Motomu Kanai
中科院分区：
文献类型：
--
作者：
Hideoki Nagai;Yuya Morita;Yohei Shimizu;Motomu Kanai
首次建立了硼化合物与温和有机碱（DBU）介导的羧酸选择性醛醇反应。在与BH3·sme2反应的氨基酸衍生物配体中包含吸电子基团，形成硼启动子，增加硼原子的刘易斯酸度，促进羧酸选择性烯酸酯形成，即使存在其他羰基，如酰胺、酯、酮或脂肪醛。显著的配体效应导致了广泛的底物范围，包括生物相关化合物。
The first carboxylic acid selective aldol reaction mediated by boron compounds and a mild organic base (DBU) was developed. Inclusion of electron-withdrawing groups in the amino acid derivative ligands reacted with BH3·SMe2forms a boron promoter with increased Lewis acidity at the boron atom and facilitated the carboxylic acid selective enolate formation, even in the presence of other carbonyl groups such as amides, esters, ketones, or aliphatic aldehydes. The remarkable ligand effect led to the broad substrate scope including biologically relevant compounds.