B(C6F5)3-Catalyzed α-Deuteration of Bioactive Carbonyl Compounds with D2O

被引：24

作者：

Chang, Yejin ^{[1
]}

Myers, Tanner ^{[1
]}

Wasa, Masayuki ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 02期

关键词：

Deuterated drug; Frustrated Lewis pair; Late-stage functionalization; Cooperative catalysis; HYDROLYTIC KINETIC RESOLUTION; ASYMMETRIC CATALYSIS; TERMINAL EPOXIDES; DRUG DISCOVERY; DEUTERIUM; EFFICIENT; TRITIUM; TRIS(PENTAFLUOROPHENYL)BORON; TRITIATION; COMPLEXES;

D O I：

10.1002/adsc.201901419

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient deuteration process of alpha-C-H bonds in various carbonyl-based pharmaceutical compounds has been developed. Catalytic reactions are initiated by the action of Lewis acidic B(C6F5)(3) and D2O, converting a drug molecule into the corresponding boron-enolate. Ensuing deuteration of the enolate by in situ-generated D2O+-H then results in the formation of alpha-deuterated bioactive carbonyl compounds with up to >98% deuterium incorporation.

引用

页码：360 / 364

页数：5

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