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Reductive CO2 Fixation via the Selective Formation of C–C Bonds: Bridging Enaminones and Synthesis of 1,4-Dihydropyridines

Authors :
Xuqiang Guo
Jinmao You
Gao Bowen
Lu Xu
Yun-Lin Liu
Yulei Zhao
Ding Xin
Feng Nan
Li Man
Zhou Zheng
Source :
Organic Letters. 22:8326-8331
Publication Year :
2020
Publisher :
American Chemical Society (ACS), 2020.

Abstract

Herein, a selective tandem C-C bond-forming reaction with CO2 was developed to realize the bridging of enaminones and synthesis of 1,4-dihydropyridines, respectively. n-Butylamine significantly promoted this CO2 deoxymethylenation procedure catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and ZnCl2. The mechanism involving the formation of bis(silyl)acetal, nucleophilic addition, and amine elimination was also interpreted to clarify the bridging of two molecules of enaminones with CO2 and the generation of dihydropyridine derivatives.

Details

ISSN :
15237052 and 15237060
Volume :
22
Database :
OpenAIRE
Journal :
Organic Letters
Accession number :
edsair.doi...........2669bcd3071caa7362507ab2d625b0ae