scholarly journals Copper-Free Alternatives to Access Ketone Building Blocks from Grignard Reagents

ACS Omega ◽  
2022 ◽  
Author(s):  
Christoph Taeschler ◽  
Eva Kirchner ◽  
Emilia Păunescu ◽  
Ulrich Mayerhöffer
Keyword(s):  
Building Blocks ◽  
Grignard Reagents

One-pot three-component polymerization for in situ generation of AIE-active poly(tetraarylethene)s using Grignard reagents as building blocks

2020 ◽  
Vol 11 (35) ◽  
pp. 5601-5609
Author(s):  
Zijie Qiu ◽  
Qingqing Gao ◽  
Ting Han ◽  
Xiaolin Liu ◽  
Jacky W. Y. Lam ◽  
...  
Keyword(s):  
Building Blocks ◽  
Grignard Reagents ◽  
One Pot ◽  
Aggregation Induced Emission ◽  
In Situ Generation

A facile polymerization route for in situ generation of polymers with aggregation-induced emission (AIE) characteristics has been developed.

Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1855-1873
Author(s):  
Senthil Narayanaperumal ◽  
Ricardo S. Schwab ◽  
Wystan K. O. Teixeira ◽  
Danilo Yano de Albuquerque
Keyword(s):  
Carbonyl Compounds ◽  
Building Blocks ◽  
Short Review ◽  
Biological Properties ◽  
Enantioselective Synthesis ◽  
Grignard Reagents ◽  
Organometallic Reagents ◽  
Important Family ◽  
Organolithium Reagents ◽  
Organozinc Reagents

Enantiomerically enriched diaryl, aryl heteroaryl, and dihetero­aryl alcohols are an important family of compounds known for their biological properties. Moreover, these molecules are highly privileged scaffolds used as building blocks for the synthesis of pharmaceutically relevant products. This short review provides background on the enantioselective arylation and heteroarylation of carbonyl compounds, as well as, the most significant improvements in this field with special emphasis on the application of organometallic reagents.1 Introduction2 Background on the Enantioselective Synthesis of Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols3 Organozinc Reagents4 Organolithium Reagents5 Grignard Reagents6 Organoaluminum Reagents7 Organotitanium Reagents8 Organobismuth Reagents9 Miscellaneous10 Conclusion

Synthesis of Optically Active Bifunctional Building Blocks through Enantioselective Copper-Catalyzed Allylic Alkylation Using Grignard Reagents

2007 ◽  
Vol 72 (7) ◽  
pp. 2558-2563 ◽  
Author(s):  
Anthoni W. van Zijl ◽  
Fernando López ◽  
Adriaan J. Minnaard ◽  
Ben L. Feringa
Keyword(s):  
Building Blocks ◽  
Optically Active ◽  
Grignard Reagents ◽  
Allylic Alkylation

scholarly journals Stereoselective Ethynylation and Propargylation of Chiral Cyclic Nitrones: Application to the Synthesis of Glycomimetics

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3339-3351 ◽  
Author(s):  
Sara García-Viñuales ◽  
Ignacio Delso ◽  
Pedro Merino ◽  
Tomás Tejero
Keyword(s):  
Dft Calculations ◽  
Click Chemistry ◽  
Experimental Error ◽  
Grignard Reagent ◽  
Building Blocks ◽  
Grignard Reagents ◽  
Propargyl Bromide ◽  
Cyclic Nitrones ◽  
Observed Behavior

Ethynylation and propargylation of chiral nonracemic polyhydroxylated cyclic nitrones with Grignard reagents are efficient methods for preparing building blocks containing an alkyne moiety to be used in copper-catalyzed azide alkyne cycloaddition click chemistry. Whereas ethynylation takes place with excellent diastereoselectivity, propargylation afforded mixtures of diastereomers in some cases. The use of (trimethylsilyl)propargyl bromide as precursor of the Grignard reagent is necessary to avoid the formation of undesired allene derivatives. DFT calculations explain, within the experimental error, the observed behavior. Cycloaddition of the obtained pyrrolidinyl alkynes with sugar azides derived from β-(1,3)-glucans provides glycomimetics suitable to be used against fungal transglycosylases.

scholarly journals Copper-catalyzed asymmetric allylic substitution reactions with organozinc and Grignard reagents

2008 ◽  
Vol 80 (5) ◽  
pp. 1025-1037 ◽  
Author(s):  
Koen Geurts ◽  
Stephen P. Fletcher ◽  
Anthoni W. van Zijl ◽  
Adriaan J. Minnaard ◽  
Ben L. Feringa
Keyword(s):  
Building Blocks ◽  
Field Work ◽  
Grignard Reagents ◽  
Allylic Alcohols ◽  
Substitution Reactions ◽  
Organometallic Reagents ◽  
Bond Forming ◽  
Allylic Alkylations ◽  
Ferrocenyl Ligands ◽  
High Yields

Asymmetric allylic alkylations (AAAs) are among the most powerful C-C bond-forming reactions. We present a brief overview of copper-catalyzed AAAs with organometallic reagents and discuss our own contributions to this field. Work with zinc reagents and phosphoramidite ligands provided a framework for later developments which employ Grignard reagents and ferrocenyl ligands. High yields and excellent regioselectivities and enantioselectivities are achieved. The AAAs may be more general than previously envisioned, in terms of using substrates functionalized with heteroatoms at various positions; heteroatom substituents at the γ-position provide densely functionalized building blocks. These h-AAA reactions rely on the design of appropriate substrates containing heteroatoms and have allowed us to demonstrate viable new approaches toward the synthesis of versatile organic building blocks. We illustrate that the chiral secondary allylic alcohols, primary homo-allylic alcohols and amines can readily be obtained in high enantiomeric purity in a catalytic asymmetric fashion by copper-catalyzed AAAs. Furthermore, we show that manipulation of the terminal olefin provides chiral building blocks where the ee of the starting materials is preserved.

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