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...

Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible Light Photoredox Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Jia-Jia Zhao ◽  
Hong-Hao Zhang ◽  
Shouyun Yu
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Chemical Transformations ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Iminium Ions ◽  
Radical Functionalization

Visible light photoredox catalysis has recently emerged as a powerful tool for the development of new and valuable chemical transformations under mild conditions. Visible-light promoted enantioselective radical transformations of imines and iminium intermediates provide new opportunities for the asymmetric synthesis of amines and asymmetric β-functionalization of unsaturated carbonyl compounds. In this review, the advance in the catalytic asymmetric radical functionalization of imines, as well as iminium intermediates, are summarized. 1 Introduction 2 The enantioselective radical functionalization of imines 2.1 Asymmetric reduction 2.2 Asymmetric cyclization 2.3 Asymmetric addition 2.4 Asymmetric radical coupling 3 The enantioselective radical functionalization of iminium ions 3.1 Asymmetric radical alkylation 3.2 Asymmetric radical acylation 4 Conclusion

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.

Asymmetric Synthesis of Homoallylamines by Nucleophilic Addition of Chirally Modified Allylboron Reagent to N-Borylimines

Synlett ◽  
1999 ◽  
Vol 1999 (12) ◽  
pp. 1987-1989 ◽  
Author(s):  
Shinichi Itsuno ◽  
Ayako Yokoi ◽  
Shizue Kuroda
Keyword(s):  
Asymmetric Synthesis ◽  
Nucleophilic Addition
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