Origin of π-facial stereoselectivity of nucleophilic addition to carbonyl compounds. Application of the exterior frontier orbital extension model to cyclohexanones with polar substituent

Tetrahedron ◽  
1999 ◽  
Vol 55 (13) ◽  
pp. 3871-3882 ◽  
Author(s):  
Shuji Tomoda ◽  
Takatoshi Senju
Keyword(s):  
Carbonyl Compounds ◽  
Nucleophilic Addition ◽  
Frontier Orbital ◽  
Polar Substituent ◽  
Extension Model

scholarly journals Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination

2014 ◽  
Vol 10 ◽  
pp. 883-889
Author(s):  
Łukasz Górecki ◽  
Artur Mucha ◽  
Paweł Kafarski
Keyword(s):  
Phosphorus Atom ◽  
Carbonyl Compounds ◽  
Nucleophilic Addition ◽  
Carbon Skeleton ◽  
Vinyl Group

The Abramov reaction, a base-catalyzed nucleophilic addition of dialkyl H-phosphonates (phosphites) to carbonyl compounds, was performed with oxidized quinine derivatives as the substrates. Homologous aldehydes obtained from the vinyl group reacted in a typical way which led to α-hydroxyphosphonates, first reported compounds containing a direct P–C bond between the quinine carbon skeleton and a phosphorus atom. For the C9 ketones a phosphonate–phosphate rearrangement, associated with a tandem elimination of the piperidine fragment, was evidenced.

Bifunctional Squaramide Catalyzed Asymmetric Synthesis of Chiral α-Mercaptosilanes

2021 ◽  
Author(s):  
Ye Zhang ◽  
Jingcheng Guo ◽  
Jinna Han ◽  
Xiangui Zhou ◽  
Wei Cao ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Nucleophilic Addition

Bifunctional squaramide-catalyzed nucleophilic addition of thiophenols to easily available β-silyl α,β-unsaturated carbonyl compounds has been successfully developed. A structurally diverse set of chiral α-mercaptosilanes was efficiently prepared in good to...

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