Asymmetric synthesis of Cyclic β-Amino Carbonyl Derivatives by a Formal [3+2] Photocycloaddition

2022 ◽  
Author(s):  
Leonardo Mollari ◽  
Miguel Valle ◽  
Ana Maria Martinez ◽  
Leyre Marzo ◽  
Alberto Fraile ◽  
...  
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Carbonyl Derivatives

Herein, a visible-light mediated strategy unlocking a family of cyclic β-amino carbonyl derivatives bearing three contiguous stereogenic centres is introduced. The overall reactivity relies on the performance of the substrate-catalyst...

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 Light-driven deracemization enabled by excited-state electron transfer

Science ◽  
2019 ◽  
Vol 366 (6463) ◽  
pp. 364-369 ◽  
Author(s):  
Nick Y. Shin ◽  
Jonathan M. Ryss ◽  
Xin Zhang ◽  
Scott J. Miller ◽  
Robert R. Knowles
Keyword(s):  
Electron Transfer ◽  
Excited State ◽  
Hydrogen Atom ◽  
Visible Light ◽  
Asymmetric Synthesis ◽  
Hydrogen Atom Transfer ◽  
Product Distributions ◽  
Reaction Proceeds ◽  
Molecular Catalysts ◽  
Distinct Approach

Deracemization is an attractive strategy for asymmetric synthesis, but intrinsic energetic challenges have limited its development. Here, we report a deracemization method in which amine derivatives undergo spontaneous optical enrichment upon exposure to visible light in the presence of three distinct molecular catalysts. Initiated by an excited-state iridium chromophore, this reaction proceeds through a sequence of favorable electron, proton, and hydrogen-atom transfer steps that serve to break and reform a stereogenic C–H bond. The enantioselectivity in these reactions is jointly determined by two independent stereoselective steps that occur in sequence within the catalytic cycle, giving rise to a composite selectivity that is higher than that of either step individually. These reactions represent a distinct approach to creating out-of-equilibrium product distributions between substrate enantiomers using excited-state redox events.

Metal free visible light driven oxidation of alcohols to carbonyl derivatives using 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) as catalyst

RSC Advances ◽  
2015 ◽  
Vol 5 (102) ◽  
pp. 84328-84333 ◽  
Author(s):  
Suvendu Samanta ◽  
Papu Biswas
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Light Irradiation ◽  
Metal Free ◽  
Carbonyl Derivatives ◽  
Oxidation Of Alcohols ◽  
Visible Light Driven ◽  
High Yields

A metal-free transformation of alcohols to the corresponding carbonyls in high yields under visible-light irradiation has been achieved at room temperature using di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) as catalyst.

Asymmetric synthesis of Au–CdSe core–semishell nanorods for plasmon-enhanced visible-light-driven hydrogen evolution

Nanoscale ◽  
2020 ◽  
Vol 12 (2) ◽  
pp. 687-694 ◽  
Author(s):  
Peng-Fei Wang ◽  
Kai Chen ◽  
Song Ma ◽  
Wei Wang ◽  
Yun-Hang Qiu ◽  
...  
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Hydrogen Evolution ◽  
Photocatalytic Properties ◽  
Cdse Core ◽  
Visible Light Driven

By controlling the content of Cd2+, lateral Au–CdSe heterorods with better photocatalytic properties under visible light were synthesized.

Enantioselective synthesis enabled by visible light photocatalysis

2020 ◽  
Vol 18 (23) ◽  
pp. 4298-4353 ◽  
Author(s):  
Bor-Cherng Hong
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Enantioselective Synthesis ◽  
Visible Light Photocatalysis ◽  
Recent Developments

This review summarizes recent developments in visible-light enantioselective photocatalysis reactions, which provide convenient and effective tools for asymmetric synthesis.

Visible light photocatalytic asymmetric synthesis of pyrrolo[1,2-a]indoles via intermolecular [3+2] cycloaddition

2019 ◽  
Vol 55 (75) ◽  
pp. 11303-11306 ◽  
Author(s):  
Antonio Casado-Sánchez ◽  
Pablo Domingo-Legarda ◽  
Silvia Cabrera ◽  
José Alemán
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Acid Catalysis ◽  
Indole Derivatives ◽  
Lewis Acid Catalysis ◽  
Visible Light Photocatalytic

The asymmetric synthesis of pyrrolo[1,2-a]indoles is developed through a [3+2] cycloaddition between silyl-indole derivatives and α,β-unsaturated N-acyl oxazolidinones by merging photocatalysis and Lewis acid catalysis.

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