Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
ERATO, Japan Science and Technology Agency, Kanai Life Science Catalysis Project, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Org Lett. 2016 May 6;18(9):2276-9. doi: 10.1021/acs.orglett.6b00914. Epub 2016 Apr 22.
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·SMe2 forms 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.
发展了一种由硼化合物和温和有机碱（DBU）介导的羧酸选择性羟醛反应。在氨基酸衍生物配体中引入吸电子基团与 BH3·SMe2 反应，形成具有增加的硼原子路易斯酸度的硼促进剂，并促进羧酸选择性烯醇盐的形成，即使在存在其他羰基化合物如酰胺、酯、酮或脂肪醛的情况下也是如此。显著的配体效应导致了广泛的底物范围，包括具有生物学相关性的化合物。
