Recent Advances in the Catalytic Asymmetric Construction of Phosphorus-Substituted Quaternary Carbon Stereocenters

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 440-469 ◽  
Author(s):  
Long Chen
Keyword(s):  
Asymmetric Synthesis ◽  
Reaction Mechanisms ◽  
Recent Progress ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Quaternary Carbon ◽  
Active Compounds ◽  
Catalytic Asymmetric Synthesis ◽  
Stereogenic Centers ◽  
Catalytic Asymmetric

Phosphorus-substituted quaternary carbon stereocenters exist widely in drugs and biologically active compounds. Catalytic asymmetric synthesis of such quaternary carbon stereogenic centers is of significant importance, with four synthetic strategies being established. This review summarizes the recent progress in this field, including the advantages and limitations of each strategy, briefly discusses the reaction mechanisms and challenges, and outlines synthetic opportunities still open.1 Introduction2 Asymmetric Hydrophosphonylation3 Asymmetric Electrophilic Phosphination4 Asymmetric Functionalization of P-Substituted Methine Compounds5 Asymmetric Addition to α-Keto- or α-Ketiminophosphonates6 Conclusion

Catalytic, Enantioselective Diamination of Alkenes

Synthesis ◽  
2021 ◽  
Author(s):  
Scott E. Denmark ◽  
Zhong-Lin Tao
Keyword(s):  
Asymmetric Synthesis ◽  
Reaction Mechanisms ◽  
Short Review ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Recent Advances ◽  
Vicinal Diamines

AbstractEnantioselective diamination of alkenes represents one of the most straightforward methods to access enantioenriched, vicinal diamines, which are not only frequently encountered in biologically active compounds, but also have broad applications in asymmetric synthesis. Although the analogous dihydroxylation of olefins is well-established, the development of enantioselective olefin diamination lags far behind. Nevertheless, several successful methods have been developed that operate by different reaction mechanisms, including a cycloaddition pathway, a two-electron redox pathway, and a radical pathway. This short review summarizes recent advances and identifies limitations, with the aim of inspiring further developments in this area.1 Introduction2 Cycloaddition Pathway3 Two-Electron Redox Pathway3.1 Pd(0)/Pd(II) Diamination3.2 Pd(II)/Pd(IV) Diamination3.3 I(I)/I(III) Diamination3.4 Se(II)/Se(IV) Diamination4 One-Electron Radical Pathway4.1 Cu-Catalyzed Diamination4.2 Fe-Catalyzed Diamination5 Summary and Outlook

scholarly journals Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Masakazu Nambo ◽  
Jacky C.-H. Yim ◽  
Luiza B. O. Freitas ◽  
Yasuyo Tahara ◽  
Zachary T. Ariki ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Recent Progress ◽  
Cross Coupling ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Arylboronic Acids ◽  
Modular Synthesis ◽  
Synthetic Routes

Abstract α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes. The ease of synthesis of fluorinated triflones as the key starting materials enables powerful late-stage transformations of known biologically active compounds into fluorinated analogs.

Catalytic asymmetric synthesis of polysubstituted spirocyclopropyl oxindoles: organocatalysis versus transition metal catalysis

2015 ◽  
Vol 2 (7) ◽  
pp. 849-858 ◽  
Author(s):  
Zhong-Yan Cao ◽  
Jian Zhou
Keyword(s):  
Transition Metal ◽  
Asymmetric Synthesis ◽  
Recent Progress ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Catalytic Asymmetric Synthesis ◽  
Versus Transition ◽  
Catalytic Asymmetric

Recent progress in catalytic asymmetric synthesis of spirocyclopropyl oxindoles via organocatalysis and transition metal catalysis are summarized and discussed.

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