ChemInform Abstract: Arylethyne Bromoboration-Negishi Coupling Route to (E)- or (Z)-Aryl-Substituted Trisubstituted Alkenes of ≥ 98% Isomeric Purity. New Horizon in the Highly Selective Synthesis of Trisubstituted Alkenes.

ChemInform ◽  
2010 ◽  
Vol 41 (29) ◽  
pp. no-no
Author(s):  
Chao Wang ◽  
Zhaoqing Xu ◽  
Tomas Tobrman ◽  
Ei-ichi Negishi
Keyword(s):  
Selective Synthesis ◽  
Negishi Coupling ◽  
Isomeric Purity ◽  
Trisubstituted Alkenes

Selective Synthesis of Enol Ethers by Nickel-Catalyzed Cross Coupling of α-oxy Vinylsulfones with Alkylzinc Reagents

2021 ◽  
Author(s):  
Liang Gong ◽  
Qian Zhang ◽  
Demeng Xie ◽  
Wei Zhang ◽  
Shiyang Xu ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Selective Synthesis ◽  
Enol Ethers ◽  
Negishi Coupling

We describe here a Ni-catalyzed Negishi coupling reaction to prepare 1,2-dialkyl enol ethers in a stereoconvergent fashion. This method employs readily available and bench-stable α-oxy-vinylsulfones as electrophiles. The C–sulfone bond...

RetroBioCat: Computer-Aided Synthesis Planning for Biocatalytic Reactions and Cascades

2020 ◽  
Author(s):  
William Finnigan ◽  
Lorna J. Hepworth ◽  
Nicholas J. Turner ◽  
Sabine Flitsch
Keyword(s):  
Organic Chemistry ◽  
Computer Aided Design ◽  
Selective Synthesis ◽  
Test Set ◽  
Synthesis Design ◽  
Computer Aided ◽  
Synthesis Planning ◽  
Enzymatic Cascades ◽  
Target Molecules ◽  
Aided Design

As the enzyme toolbox for biocatalysis has expanded, so has the potential for the construction of powerful enzymatic cascades for efficient and selective synthesis of target molecules. Additionally, recent advances in computer-aided synthesis planning (CASP) are revolutionizing synthesis design in both synthetic biology and organic chemistry. However, the potential for biocatalysis is not well captured by tools currently available in either field. Here we present RetroBioCat, an intuitive and accessible tool for computer-aided design of biocatalytic cascades, freely available at retrobiocat.com. Our approach uses a set of expertly encoded reaction rules encompassing the enzyme toolbox for biocatalysis, and a system for identifying literature precedent for enzymes with the correct substrate specificity where this is available. Applying these rules for automated biocatalytic retrosynthesis, we show our tool to be capable of identifying promising biocatalytic pathways to target molecules, validated using a test-set of recent cascades described in the literature.

Enantioselective Synthesis of Azamerone

2018 ◽  
Author(s):  
Matthew L. Landry ◽  
Grace McKenna ◽  
Noah Burns
Keyword(s):  
Late Stage ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Selective Synthesis

A concise and selective synthesis of the dichlorinated meroterpenoid azamerone is described. The paucity of tactics for the synthesis of chiral organochlorides motivated the development of unique strategies for accessing these motifs in enantioenriched forms. The route features a novel enantioselective chloroetherification reaction, a Pd-catalyzed cross-coupling between a quinone diazide and a boronic hemiester, and a late-stage tetrazine [4+2]-cycloaddition/oxidation cascade.

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