Silyl enol ethers in Paternò-Büchi reactions. Functional group tolerance and the effect of β-alkyl substitution

1995 ◽  
Vol 1995 (5) ◽  
pp. 855-865 ◽  
Author(s):  
Thorsten Bach
Keyword(s):  
Functional Group ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Alkyl Substitution

scholarly journals Direct Access to Mono-Protected Homoallylic 1,2-Diols via Dual Chromium/ Photoredox Catalysis

2020 ◽  
Author(s):  
Felix Schäfers ◽  
Linda Quach ◽  
J. Luca Schwarz ◽  
Mar Saladrigas ◽  
Constantin G. Daniliuc ◽  
...  
Keyword(s):  
Functional Group ◽  
Protecting Groups ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Efficient Synthesis ◽  
Enol Ethers ◽  
Silyl Enol Ethers

<p>A dual catalytic strategy enables the efficient synthesis of mono-protected homoallylic 1,2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct access to this important motif without the (super)stoichiometric use of prefunctionalized metal-allyl species. A variety of silyl- and alkyl-based protecting groups is shown and functional group tolerance, chemoselectivity and scalability are highlighted. </p>

scholarly journals Direct Access to Mono-Protected Homoallylic 1,2-Diols via Dual Chromium/ Photoredox Catalysis

2020 ◽  
Author(s):  
Felix Schäfers ◽  
Linda Quach ◽  
J. Luca Schwarz ◽  
Mar Saladrigas ◽  
Constantin G. Daniliuc ◽  
...  
Keyword(s):  
Functional Group ◽  
Protecting Groups ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Efficient Synthesis ◽  
Enol Ethers ◽  
Silyl Enol Ethers

<p>A dual catalytic strategy enables the efficient synthesis of mono-protected homoallylic 1,2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct access to this important motif without the (super)stoichiometric use of prefunctionalized metal-allyl species. A variety of silyl- and alkyl-based protecting groups is shown and functional group tolerance, chemoselectivity and scalability are highlighted. </p>

scholarly journals Direct Access to Mono-Protected Homoallylic 1,2-Diols via Dual Chromium/ Photoredox Catalysis

2020 ◽  
Author(s):  
Felix Schäfers ◽  
Linda Quach ◽  
J. Luca Schwarz ◽  
Mar Saladrigas ◽  
Constantin G. Daniliuc ◽  
...  
Keyword(s):  
Functional Group ◽  
Protecting Groups ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Efficient Synthesis ◽  
Enol Ethers ◽  
Silyl Enol Ethers

<p>A dual catalytic strategy enables the efficient synthesis of mono-protected homoallylic 1,2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct access to this important motif without the (super)stoichiometric use of prefunctionalized metal-allyl species. A variety of silyl- and alkyl-based protecting groups is shown and functional group tolerance, chemoselectivity and scalability are highlighted. </p>

scholarly journals Versatile and Ligand-Free Copper-Catalyzed α-Arylations of Aromatic Ketones Using Diaryliodonium Salts

2021 ◽  
Author(s):  
Maxime Bouquin ◽  
Florian Jaroschik ◽  
Marc Taillefer
Keyword(s):  
Functional Group ◽  
Catalyst Loading ◽  
Synthetic Methodology ◽  
Enol Ethers ◽  
Aromatic Ketones ◽  
Silyl Enol Ethers ◽  
Diaryliodonium Salts ◽  
Ligand Free ◽  
Low Catalyst Loading

A ligand and base free copper catalyzed synthetic methodology for the efficient alpha-arylation of aromatic ketones has been developed. The reaction of the ketone-derived silyl enol ethers with diaryliodonium salts led to the intermolecular C-C coupling displaying high functional group tolerance with a low catalyst loading.<br>

scholarly journals Versatile and Ligand-Free Copper-Catalyzed α-Arylations of Aromatic Ketones Using Diaryliodonium Salts

2021 ◽  
Author(s):  
Maxime Bouquin ◽  
Florian Jaroschik ◽  
Marc Taillefer
Keyword(s):  
Functional Group ◽  
Catalyst Loading ◽  
Synthetic Methodology ◽  
Enol Ethers ◽  
Aromatic Ketones ◽  
Silyl Enol Ethers ◽  
Diaryliodonium Salts ◽  
Ligand Free ◽  
Low Catalyst Loading

A ligand and base free copper catalyzed synthetic methodology for the efficient alpha-arylation of aromatic ketones has been developed. The reaction of the ketone-derived silyl enol ethers with diaryliodonium salts led to the intermolecular C-C coupling displaying high functional group tolerance with a low catalyst loading.<br>

Addition of Allylsilanes and Silyl Enol Ethers to Small Oxygenated Rings: New Tools for Organic Synthesis

2014 ◽  
Vol 18 (5) ◽  
pp. 525-546 ◽  
Author(s):  
Carmen Hernandez-Cervantes ◽  
Miriam Alvarez-Corral ◽  
Manuel Munoz-Dorado ◽  
Ignacio Rodriguez-Garcia
Keyword(s):  
Organic Synthesis ◽  
Enol Ethers ◽  
Silyl Enol Ethers

Bench‐Stable Electrophilic Fluorinating Reagents for Highly Selective Mono‐ and Difluorination of Silyl Enol Ethers

2021 ◽  
Author(s):  
Kohsuke Aikawa ◽  
KyoKo Nozaki ◽  
Takashi Okazoe ◽  
Yuichiro Ishibashi ◽  
Akiya Adachi
Keyword(s):  
Enol Ethers ◽  
Silyl Enol Ethers
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