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不对称有机催化同系化反应:获得多样手性三氟甲基有机硼物种的途径。

Asymmetric Organocatalytic Homologation: Access to Diverse Chiral Trifluoromethyl Organoboron Species.

机构信息

Department of Organic Chemistry, Stockholm University, SE-106 91, Stockholm, Sweden.

Department of Materials and Environmental Chemistry, Stockholm University, SE106 91, Stockholm, Sweden.

出版信息

Chemistry. 2022 Oct 18;28(58):e202202059. doi: 10.1002/chem.202202059. Epub 2022 Aug 18.

Abstract

A broad range of aliphatic, aromatic, and heterocyclic boronic acids were successfully homologated using trifluorodiazoethane in the presence of BINOL derivatives to provide the corresponding chiral trifluoromethyl containing boronic acid derivatives in high yields and excellent enantioselectivity. The in situ conversion of the chiral transient boronic acids to the corresponding alcohols or β-CF3 carboxylates are also demonstrated.

摘要

使用三氟重氮乙烷,在 BINOL 衍生物的存在下,成功地同系化了广泛的脂肪族、芳香族和杂环硼酸,以高收率和优异的对映选择性提供了相应的手性三氟甲基硼酸衍生物。还证明了手性瞬态硼酸的原位转化为相应的醇或β-CF3 羧酸酯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fea/9804810/d56ace7b6e38/CHEM-28-0-g006.jpg

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