Rongalite-Mediated Transition Metal- and Hydride-Free Chemoselective Reduction of a-Keto Esters and a-Keto Amides

被引：20

作者：

Golla, Sivaparwathi ^{[1
]}

Kokatla, Hari Prasad ^{[1
]}

机构：

[1] Natl Inst Technol Warangal, Dept Chem, Warangal 506004, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 15期

关键词：

ALPHA-HYDROXY AMIDES; CATALYZED SELECTIVE SYNTHESIS; ACTIVATED CARBONYL GROUPS; TRANSFER HYDROGENATION; ACID-DERIVATIVES; ENANTIOSELECTIVE SYNTHESIS; BENZOSULTINE-SULFONE; GREEN REAGENT; ONE-POT; HYDROSILYLATION;

D O I：

10.1021/acs.joc.2c00936

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition metal-and hydride-free protocol has been developed for the chemoselective reduction of alpha-keto esters and alpha- keto amides using rongalite as a reducing agent. Here, rongalite acts as a hydride-free reducing agent via a radical mechanism. This protocol offers the synthesis of a wide range of alpha-hydroxy esters and alpha-hydroxy amides with 85-98% yields. This chemoselective method is compatible with other reducible functionalities such as halides, alkenes, amides, and nitriles. The use of inexpensive rongalite (ca. $0.03/1 g), mild reaction conditions, and gram-scale synthesis are some of the key features of this methodology. Also, cyclandelate, a vasodilator drug, has been synthesized in gram scale with 79% yield.

引用

页码：9915 / 9925

页数：11

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