Extremely Efficient Chiral Induction in Conjugate Additions ofp-Tolyl α-Lithio-β-(trimethylsilyl)ethyl Sulfoxide and Subsequent Electrophilic Trapping Reactions

2000 ◽  
Vol 65 (6) ◽  
pp. 1758-1766 ◽  
Author(s):  
Shuichi Nakamura ◽  
Yoshihiko Watanabe ◽  
Takeshi Toru
Keyword(s):  
Conjugate Additions ◽  
Chiral Induction ◽  
Trapping Reactions ◽  
Ethyl Sulfoxide

Conjugate Additions of Organolithiums to Electron-poor Olefins: A Simple and Useful Approach to the Synthesis of Complex Molecules

2016 ◽  
Vol 21 (3) ◽  
pp. 190-217 ◽  
Author(s):  
Paola Vitale ◽  
Vito Capriati ◽  
Saverio Florio ◽  
Filippo Perna ◽  
Antonio Salomone
Keyword(s):  
Conjugate Additions ◽  
Complex Molecules

scholarly journals Asymmetric Catalysis with MOFs Prepared via Chiral Induction Effect

Synfacts ◽  
2010 ◽  
Vol 2011 (01) ◽  
pp. 0105-0105
Author(s):  
C. Duan ◽  
D. Dang ◽  
P. Wu ◽  
C. He ◽  
Z. Xie
Keyword(s):  
Asymmetric Catalysis ◽  
Induction Effect ◽  
Chiral Induction

Synthetic Strategies to Access Heteroatomic Spirocentres Embedded in Natural Products

Synthesis ◽  
2021 ◽  
Author(s):  
Michael P. Badart ◽  
Bill C. Hawkins
Keyword(s):  
Natural Products ◽  
Heterocyclic Compound ◽  
Chemical Space ◽  
Three Dimensional ◽  
Coupling Reactions ◽  
Conjugate Additions ◽  
Biological Targets ◽  
Compound Libraries ◽  
The Common ◽  
Significant Attention

AbstractThe spirocyclic motif is abundant in natural products and provides an ideal three-dimensional template to interact with biological targets. With significant attention historically expended on the synthesis of flat-heterocyclic compound libraries, methods to access the less-explored three-dimensional medicinal-chemical space will continue to increase in demand. Herein, we highlight by reaction class the common strategies used to construct the spirocyclic centres embedded in a series of well-studied natural products.1 Introduction2 Cycloadditions3 Palladium-Catalysed Coupling Reactions4 Conjugate Additions5 Imines, Aminals, and Hemiaminal Ethers6 Mannich-Type Reactions7 Oxidative Dearomatisation8 Alkylation9 Organometallic Additions10 Conclusions

Catch It If You Can: Copper-Catalyzed (Transfer) Hydrogenation Reactions and Coupling Reactions by Intercepting Reactive Intermediates Thereof

Synthesis ◽  
2020 ◽  
Vol 52 (17) ◽  
pp. 2483-2496
Author(s):  
Johannes F. Teichert ◽  
Lea T. Brechmann
Keyword(s):  
Coupling Reaction ◽  
Reactive Intermediates ◽  
Transfer Hydrogenation ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Starting Point ◽  
Bond Forming Reactions ◽  
Hydrogenation Reactions ◽  
Multicomponent Coupling Reactions ◽  
Trapping Reactions

The key reactive intermediate of copper(I)-catalyzed alkyne semihydrogenations is a vinylcopper(I) complex. This intermediate can be exploited as a starting point for a variety of trapping reactions. In this manner, an alkyne semihydrogenation can be turned into a dihydrogen­-mediated coupling reaction. Therefore, the development of copper-catalyzed (transfer) hydrogenation reactions is closely intertwined with the corresponding reductive trapping reactions. This short review highlights and conceptualizes the results in this area so far, with H2-mediated carbon–carbon and carbon–heteroatom bond-forming reactions emerging under both a transfer hydrogenation setting as well as with the direct use of H2. In all cases, highly selective catalysts are required that give rise to atom-economic multicomponent coupling reactions with rapidly rising molecular complexity. The coupling reactions are put into perspective by presenting the corresponding (transfer) hydrogenation processes first.1 Introduction: H2-Mediated C–C Bond-Forming Reactions2 Accessing Copper(I) Hydride Complexes as Key Reagents for Coupling Reactions; Requirements for Successful Trapping Reactions 3 Homogeneous Copper-Catalyzed Transfer Hydrogenations4 Trapping of Reactive Intermediates of Alkyne Transfer Semi­hydrogenation Reactions: First Steps Towards Hydrogenative Alkyne Functionalizations 5 Copper(I)-Catalyzed Alkyne Semihydrogenations6 Copper(I)-Catalyzed H2-Mediated Alkyne Functionalizations; Trapping of Reactive Intermediates from Catalytic Hydrogenations6.1 A Detour: Copper(I)-Catalyzed Allylic Reductions, Catalytic Generation of Hydride Nucleophiles from H2 6.2 Trapping with Allylic Electrophiles: A Copper(I)-Catalyzed Hydro­allylation Reaction of Alkynes 6.3 Trapping with Aryl Iodides7 Conclusion

Sign in / Sign up

Export Citation Format

Share Document