Asymmetric Synthesis of SCF3-Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes

被引：1

作者：

Kojima, Yuki ^{[1
]}

Nishii, Yuji ^{[1
]}

Hirano, Koji ^{[1
,2
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Inst Open & Transdisciplinary Res Initiat ICS OTRI, Innovat Catalysis Sci Div, Suita, Osaka 5650871, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2024年 / 63卷 / 24期

基金：

日本学术振兴会;

关键词：

asymmetric catalysis; copper; fluorine molecule; hydrofunctionalization; trifluoromethylthio group; BORONIC ESTERS; MEDIATED TRIFLUOROMETHYLTHIOLATION; ENANTIOSELECTIVE CONSTRUCTION; SUBSTITUENT CONSTANTS; ACIDS; FLUORINE; ALKENES; PHARMACEUTICALS; HYDROAMINATION; ALCOHOLS;

D O I：

10.1002/anie.202403337

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A synthetic method for preparation of optically active trifluoromethylthio (SCF3) compounds by a copper-catalyzed regio- and enantioselective hydroboration of 1-trifluoromethylthioalkenes with H-Bpin has been developed. The enantioselective hydrocupration of an in situ generated CuH species and subsequent boration reaction generate a chiral SCF3-containing alkylboronate, of which Bpin moiety can be further transformed to deliver various optically active SCF3 molecules. Computational studies suggest that the SCF3 group successfully controls the regioselectivity in the reaction.

引用

页数：6

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