Photoredox-Catalyzed Giese Reactions: Decarboxylative Additions to Cyclic Vinylogous Amides and Esters.

Kevin Dykstra,Jeffrey T Kuethe,Alexei Buevich,Qi Gao,Yu-Hong Lam

doi:10.3390/molecules27020417

Abstract

An effective strategy has been developed for the photoredox-catalyzed decarboxylative addition of cyclic amino acids to both vinylogous amides and esters leading to uniquely substituted heterocycles. The additions take place exclusively trans to the substituent present on the dihydropyridone ring affording stereochemical control about the new carbon-carbon bond. These reactions are operationally simplistic and afford the desired products in good to excellent isolated yields.

Highlights

Reductive addition of carbon-centered radicals to electron-deficient olefins, known as the Giese reaction, has been utilized in a number of synthetic applications including totalAdditions to Cyclic Vinylogous syntheses [1,2,3,4,5,6,7]
Recent molecules27020417 examples of carbon-centered radicals utilized in the Giese reaction have been generated via carboxylic acids [8,9,10], trifluoroborate salts [11,12], secondary and tertiary alcohols [13,14,15], Academic Editors: Damian organosilicates [16,17,18], alkyl halides [19], and via triplet enone diradicals [20]
Our investigations began by examining the reaction between dihydropyridone 5 [21]

Summary

Introduction

Reductive addition of carbon-centered radicals to electron-deficient olefins, known as the Giese reaction, has been utilized in a number of synthetic applications including totalAdditions to Cyclic Vinylogous syntheses [1,2,3,4,5,6,7]. Reductive addition of carbon-centered radicals to electron-deficient olefins, known as the Giese reaction, has been utilized in a number of synthetic applications including total. Molecules 2022, deal of interest in recent years as a valuable method for the construction of carbon-carbon. Recent molecules27020417 examples of carbon-centered radicals utilized in the Giese reaction have been generated via carboxylic acids [8,9,10], trifluoroborate salts [11,12], secondary and tertiary alcohols [13,14,15], Academic Editors: Damian organosilicates [16,17,18], alkyl halides [19], and via triplet enone diradicals [20]. A. Luzzio method for the construction of carbon-carbon bonds leading to the formation of molecules

Methods

Results

Conclusion