Four-Component Reaction Access to Nitrile-Substituted All-Carbon Quaternary Centers

Author(s):  
Xin Hu ◽  
Qiang Bian ◽  
Zheng-Lin Wang ◽  
Lin-Jie Guo ◽  
Yi-Ze Xu ◽  
...  
Keyword(s):  
2020 ◽  
Author(s):  
José Tiago Menezes Correia ◽  
Gustavo Piva da Silva ◽  
Camila Menezes Kisukuri ◽  
Elias André ◽  
Bruno Pires ◽  
...  

A metal- and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donor-aceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. <a>The method provides an operationally simple, robust and step-economical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential one-pot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches</a>.


2018 ◽  
Author(s):  
Reece Jacques ◽  
Robert D. C. Pullin ◽  
Stephen P. Fletcher

<div> <div> <div> <p>A highly regio-, diastereo- and enantioselective Cu-catalyzed desymmetrization of diverse meso-bisphosphates with alkyl zirconium nucleophiles has been developed. The reaction allows access to a broad range of functionalized cyclopentenes with up to three contiguous stereogenic centers, including quaternary centers and spirocyclic ring systems.</p></div></div></div>


2018 ◽  
Author(s):  
Reece Jacques ◽  
Robert D. C. Pullin ◽  
Stephen P. Fletcher

<div> <div> <div> <p>A highly regio-, diastereo- and enantioselective Cu-catalyzed desymmetrization of diverse meso-bisphosphates with alkyl zirconium nucleophiles has been developed. The reaction allows access to a broad range of functionalized cyclopentenes with up to three contiguous stereogenic centers, including quaternary centers and spirocyclic ring systems.</p></div></div></div>


2019 ◽  
Author(s):  
Sebastien Alazet ◽  
Michael West ◽  
Purvish Patel ◽  
Sophie Rousseaux

The efficient preparation of nitrile-containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non-toxic sources of CN. Herein, we report that 2-methyl-2-phenylpropanenitrile is an efficient, non-toxic, electrophilic CN source for the synthesis of nitrile-bearing quaternary centers via a thermodynamic transnitrilation and anion-relay strategy. This one-pot process leads to nitrile products resulting from the gem-difunctionalization of alkyl lithium reagents.<br>


2021 ◽  
Vol 8 (7) ◽  
pp. 1447-1453
Author(s):  
Jiang Lou ◽  
Wenjia Han ◽  
Zhuqing Liu ◽  
Jiaqi Xiao

Rhodium(iii)-catalyzed enone carbonyl directed C–H activation/annulation of α-aroyl ketene dithioacetals with diazo compounds has been realized for the synthesis of β-quaternary indanones.


2021 ◽  
Vol 86 (6) ◽  
pp. 4598-4606
Author(s):  
Jiandong Guo ◽  
Wu Yang ◽  
Dongju Zhang ◽  
Shou-Guo Wang ◽  
Xiaotai Wang
Keyword(s):  

2008 ◽  
Vol 10 (13) ◽  
pp. 2637-2640 ◽  
Author(s):  
Claudio Palomo ◽  
Mikel Oiarbide ◽  
Jesús M. García ◽  
Patricia Bañuelos ◽  
José M. Odriozola ◽  
...  

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