Creation of contiguous quaternary centers by way of [3,3] sigmatropic rearrangements: synthesis of trichodiene and bazzanene

1986 ◽  
Vol 51 (23) ◽  
pp. 4485-4488 ◽  
Author(s):  
John C. Gilbert ◽  
Terence A. Kelly
Keyword(s):  
Quaternary Centers ◽  
Sigmatropic Rearrangements

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

2020 ◽  
Author(s):  
José Tiago Menezes Correia ◽  
Gustavo Piva da Silva ◽  
Camila Menezes Kisukuri ◽  
Elias André ◽  
Bruno Pires ◽  
...  
Keyword(s):  
Electron Donor ◽  
Functional Group ◽  
Photoexcited Electron ◽  
One Pot ◽  
Quaternary Centers ◽  
Metal Free ◽  
Acceptor Complex ◽  
Catalyst Free ◽  
Donor Acceptor ◽  
Radical Cascade

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>.

Diverse Cyclopentenes via Enantioselective Cu-Catalyzed Desymmetrization

2018 ◽  
Author(s):  
Reece Jacques ◽  
Robert D. C. Pullin ◽  
Stephen P. Fletcher
Keyword(s):  
Ring Systems ◽  
Quaternary Centers ◽  
Stereogenic Centers

<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>

Diverse Cyclopentenes via Enantioselective Cu-Catalyzed Desymmetrization

2018 ◽  
Author(s):  
Reece Jacques ◽  
Robert D. C. Pullin ◽  
Stephen P. Fletcher
Keyword(s):  
Ring Systems ◽  
Quaternary Centers ◽  
Stereogenic Centers

<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>

Synthesis of Nitrile-Bearing Quaternary Centers via an Equilibrium-Driven Transnitrilation and Anion-Relay Strategy

2019 ◽  
Author(s):  
Sebastien Alazet ◽  
Michael West ◽  
Purvish Patel ◽  
Sophie Rousseaux
Keyword(s):  
Building Blocks ◽  
One Pot ◽  
Quaternary Centers ◽  
Synthetic Intermediates

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>

Rhodium-catalyzed enone carbonyl directed C–H activation for the synthesis of indanones containing all-carbon quaternary centers

2021 ◽  
Vol 8 (7) ◽  
pp. 1447-1453
Author(s):  
Jiang Lou ◽  
Wenjia Han ◽  
Zhuqing Liu ◽  
Jiaqi Xiao
Keyword(s):  
Diazo Compounds ◽  
Quaternary Centers ◽  
Ketene Dithioacetals

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.

Mechanistic Insights into Formation of All-Carbon Quaternary Centers via Scandium-Catalyzed C–H Alkylation of Imidazoles with 1,1-Disubstituted Alkenes

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