Organocatalytic α-Allylation of α-Branched Aldehydes by Synergistic Catalysis of Brønsted Acids and Amines

2016 ◽  
Vol 2016 (28) ◽  
pp. 4768-4772 ◽  
Author(s):  
Filip Stanek ◽  
Maciej Stodulski
Keyword(s):  
Bronsted Acids ◽  
Synergistic Catalysis

A highly enantioselective Mannich reaction of aldehydes with cyclic N-acyliminium ions by synergistic catalysis

2015 ◽  
Vol 51 (71) ◽  
pp. 13694-13697 ◽  
Author(s):  
Francesco Berti ◽  
Federico Malossi ◽  
Fabio Marchetti ◽  
Mauro Pineschi
Keyword(s):  
Secondary Amine ◽  
Mannich Reaction ◽  
Enantioselective Synthesis ◽  
Bronsted Acids ◽  
Acyliminium Ions ◽  
Synergistic Catalysis

A novel enantioselective synthesis of carbamoyl isoquinoline and tetrahydropyridine derivatives is accomplished using matched combinations of Lewis or Brønsted acids and secondary amine organocatalysts.

Regio-, Stereo- and Enantioselective α-Addition of Carbonyl Nucleo-philes to Allenamides Catalyzed by a Synergistic Copper/Enamine System

2020 ◽  
Author(s):  
Rémi Blieck ◽  
Sebastien Lemouzy ◽  
Marc Taillefer ◽  
Florian Monnier
Keyword(s):  
Catalytic System ◽  
Secondary Amine ◽  
Primary Amine ◽  
Synergistic Catalysis ◽  
Enantioselective Addition ◽  
Amine Catalysts

A dual copper/enamine catalytic system is found to enable an intermolecular enantioselective α-addition of various carbonyl nucleophiles to allenamides. Secondary amine catalysts allowed the highly enantioselective addition of aldehydes, while using primary amine catalysts led to the enantioselective addition of ketoester nucleophiles. The process was found to be highly regio-, stereo- and enantio-selective and represented the first allene hydrofunctionalization using an synergistic catalysis involving copper

One-Pot Synthesis and Conformational Analysis of 6-Membered Cyclic Iodonium Salts

2020 ◽  
Author(s):  
Lucien Caspers ◽  
Julian Spils ◽  
Mattis Damrath ◽  
Enno Lork ◽  
Boris Nachtsheim
Keyword(s):  
Conformational Analysis ◽  
Bronsted Acids ◽  
One Pot ◽  
Benzyl Alcohols ◽  
Iodonium Salts ◽  
Efficient Approach ◽  
One Pot Synthesis ◽  
Diaryliodonium Salts

In this article we describe an efficient approach for the synthesis of cyclic diaryliodonium salts. The method is based on benzyl alcohols as starting materials and consists of an Friedel-Crafts-arylation/oxidation sequence. Besides a deep optimization, particluar focusing on the choice and ratios of the utilized Bronsted-acids and oxidants, we explore the substrate scope of this transformation. We also discuss an interesting isomerism of cyclic iodonium salts substituted with aliphatic substituents at the bridge head carbon. <br>

scholarly journals Site-specific Umpolung amidation of carboxylic acids via triplet synergistic catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yunyun Ning ◽  
Shuaishuai Wang ◽  
Muzi Li ◽  
Jie Han ◽  
Chengjian Zhu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Amide Bond ◽  
Coupling Reagents ◽  
Complex Molecules ◽  
Bond Forming ◽  
Synergistic Catalysis ◽  
Wide Range ◽  
Amidation Reaction ◽  
Forming Methods

AbstractDevelopment of catalytic amide bond-forming methods is important because they could potentially address the existing limitations of classical methods using superstoichiometric activating reagents. In this paper, we disclose an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by the triplet synergistic catalysis of FeI2, P(V)/P(III) and photoredox catalysis, which avoids the production of byproducts from stoichiometric coupling reagents. A wide range of carboxylic acids, including aliphatic, aromatic and alkenyl acids participate smoothly in such reactions, generating structurally diverse amides in good yields (86 examples, up to 97% yield). This Umpolung amidation strategy opens a method to address challenging regioselectivity issues between nucleophilic functional groups, and complements the functional group compatibility of the classical amidation protocols. The synthetic robustness of the reaction is demonstrated by late-stage modification of complex molecules and gram-scale applications.

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