Abstract Although isocyanide‐based multicomponent reactions (MCRs), introduced in 1921 by Passerini, largely predominate nowadays the construction of widely diverse heterocycles, one first substrate classes involved a MCR was that 1,3‐dicarbonyl derivatives, with Hantzsch’s dihydropyridine synthesis appearing as early 1882. The aim this microreview is to present an overview great synthetic potential MCRs involving specific reactivity easily accessible derivatives and stress their more recent...

For the first time, enantiomerically enriched atropoisomeric furans have been accessed using a central-to-axial chirality conversion strategy. Hence, oxidation of enantioenriched dihydrofuran precursors gave rise to axially chiral with high enantiopurities accounting from excellent percentages (cp) in most cases.

We describe a new multicomponent domino reaction from beta-ketoamides, involved as substrates and nucleophilic partners. obtain highly functionalized original 2,6-diazabicyclo[2.2.2]octane cores (2,6-DABCO) in five-step one-pot sequence, which is fast, environmentally friendly, operationally simple to manage, combines step- atom-economic aspects.

Abstract Suitably substituted enantioenriched 4‐aryl‐1,4‐dihydro‐pyridines prepared by an organocatalytic enantioselective Michael addition were oxidized with MnO 2 into axially chiral 4‐arylpyridines central‐to‐axial chirality conversion. Moderate to complete percentages ( cp ) observed, and a model for the conversion of is discussed.

Three is a lucky number: An enantioselective transformation of allylic alcohols into β-chiral saturated has been developed by combining two distinct metal- and organocatalyzed catalytic cycles. This waste-free triple cascade process merges an iron-catalyzed borrowing-hydrogen step with aminocatalyzed nucleophilic addition reaction.

Abstract The aim of this mini‐review is to present an overview the high synthetic potential Multicomponent Reactions (MCRs) involving specific reactivity easily accessible 1,3‐dicarbonyl derivatives. contribution only focuses on sequences in which first step consists a Michael addition. Recent developments these new useful methodologies valuable for selective construction highly functionalized heterocycles value are surveyed.

The first organocatalytic enantio- and diastereoselective conjugate addition of α-ketoamides to nitroalkenes has been achieved using a bifunctional amino thiourea catalyst. In this new approach, the substrate amide proton plays critical role in formation Michael anti-adducts high yields stereoselectivities. To illustrate synthetic potential methodology, diastereo- enantioselective synthesis hexasubstituted cyclohexane via Michael-Michael-Henry cascade reaction is described.

Abstract Although long known, 1,2‐ and 1,3‐dicarbonyl compounds have recently come more to prevalence as ideal substrates for the invention of new stereoselective multiple bond‐forming transformations (MBFTs). Herein, a critical appraisal is presented some most spectacular these MBFTs, which allow formation from three up six bonds in highly step‐ atom‐economical processes.

Polysubstituted chiral cyclohexanes and cyclohexenes are important building blocks in organic synthesis. From historical pioneering reports to the most recent accounts, this review focuses on domino enantioselective organocatalytic methodologies that have allowed control of relative absolute configurations up six stereogenic centers construction these versatile molecular architectures. 1 Introduction 2 Two-Component Transformations 2.1 Michael-Initiated Domino Reactions with α,β-Unsaturated...

Abstract Suitably substituted enantioenriched 4‐aryl‐1,4‐dihydro‐pyridines prepared by an organocatalytic enantioselective Michael addition were oxidized with MnO 2 into axially chiral 4‐arylpyridines central‐to‐axial chirality conversion. Moderate to complete percentages ( cp ) observed, and a model for the conversion of is discussed.

A detailed study of the enantioselective borrowing hydrogen functionalization allylic alcohols has allowed us to improve our understanding reaction parameters affecting both rate and enantiocontrol. This subsequently led identification a triple catalysis combination iron catalysts, copper organocatalysts. By this cooperative action among three distinct activation modes, wide variety have been functionalized in improved typical 90% ee, providing rapid access crucial synthetic building blocks.

ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTA Practical Method for the Large-Scale Synthesis of Diastereomerically Pure (2R,5S)- 3-Phenyl-2-(8-quinolinoxy)- 1,3-diaza-2-phosphabicyclo-[3.3.0]-octane Ligand (QUIPHOS). and X-ray Structure Its Corresponding Chiral π-Allyl Palladium ComplexJean Michel Brunel, Thierry Constantieux, Gérard BuonoView Author Information E.N.S.S.P.I.C.A.M., UMR 6516 CNRS, Faculté de St Jérôme, Av. Escadrille Normandie Niemen, 13397 Marseille, Cedex 20, France Cite this:...

A simple metal-free, step-economic and selective access to pyridines from readily available substrates is reported, involving a flexible 4 Å molecular sieves promoted Michael addition initiated domino three-component reaction between 1,3-dicarbonyl, acceptor synthetic equivalent of ammonia.

Abstract Synthetic applications of cyclobutanones other than ring expansion and fragmentation reactions are rare. Herein, highly efficient diastereo‐ enantioselective organocatalytic Michael additions 2‐substituted cyclobutanone derivatives to nitroalkenes reported allowing the stereocontrolled creation ‘all‐carbon’ quaternary centers. The approach relies on both use Brønsted base/hydrogen‐bond donor bifunctional organocatalysts, importantly, specific stabilization activation with a...

Abstract A metal‐free and completely regioselective three‐component synthesis of highly functionalized pyridines from 1,3‐dicarbonyl derivatives Michael acceptors has been achieved. Activated acceptors, that is, β,γ‐unsaturated α‐oxo carbonyl derivatives, were utilized, allowing substitution at the 4‐position remarkable functional diversity 2‐position pyridine ring. The scope limitations this environmentally friendly domino reaction are disclosed, with full experimental data, results...

An unprecedented cascade reaction combining dual iron–amine-catalyzed enantioselective functionalization of allylic alcohols and chemoselective acyl transfer is presented. It allows, from diketones alcohols, preparation efficiently functionalized γ-chiral in up to 96% yield 96:4 er. The interest this redox-, atom-, step-economomical approach was further demonstrated the short synthesis several key fragments biologically active natural products or odorant molecules.

Aller guten Dinge sind drei: Durch die Verbindung zweier metall- und organokatalysierter Katalysezyklen wurde eine enantioselektive Umsetzung von allylischen Alkoholen zu β-chiralen gesättigten entwickelt. Dieser abfallfreie dreifache Kaskadenprozess kombiniert einen Eisen-katalysierten Borrowing-Hydrogen-Schritt mit einer Amin-katalysierten nucleophilen Addition.

Abstract α,β‐Unsaturated acyl cyanides are key bis‐electrophile substrates for successful domino enantioselective organocatalyzed Michael‐intramolecular acylation sequences. This new reactivity has been applied to the synthesis of enantioenriched azaspiro[4,5]decanone ring systems by a formal [3+3]spiroannulation, constituting rare example glutarimides in an optically active form.

Versatile partners: α-Ketocarbonyls have been shown for the first time to be versatile partners in a Michael addition promoted oxidative domino three-component reaction under heterogeneous conditions. This multicomponent sequence led development of general synthesis highly functionalized pyridines (see scheme), allowing selective and simultaneous incorporation substituent at 4-position synthetically useful functionality strategic 2-position.

The secondary amido group of α-substituted β-ketoamides plays a crucial role in the control reactivity and spatial arrangement (selectivity) organocatalyzed Michael addition to unsaturated carbonyls. This results an unprecedented activation mode substrates through H-bonding interactions allowing construction enantiomerically enriched functionalized all-carbon quaternary centers spiroaminals high synthetic potential.