Nickel-catalyzed enantioselective arylation of pyridine

Lutz, Jean‐François; Chau, Stephen T.; Doyle, Abigail G.

doi:10.1039/c6sc00702c

Cited by 73 publications

(37 citation statements)

References 44 publications

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“… 17 Although early methods utilised stoichiometric chiral auxiliaries 18 and preformed nucleophiles 19 to impart stereoselectivity, recent advances have focused on the development of catalytic enantioselective protocols. Transition metal-catalysed dearomatisation reactions of pyridines 20 have been achieved using various nucleophiles (cyanide, 20 a alkyne, 20 b , c , h alkyl/aryl zinc) 20 d , f , j however these typically yield the C(2)- or C(6)-addition products. In recent years, a number of effective organocatalytic strategies for pyridinium dearomatisation have been demonstrated ( Scheme 2B ).…”

Section: Introductionmentioning

confidence: 99%

Catalytic enantioselective synthesis of 1,4-dihydropyridines via the addition of C(1)-ammonium enolates to pyridinium salts

et al. 2021

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Section: Introductionmentioning

confidence: 99%

Catalytic enantioselective synthesis of 1,4-dihydropyridines via the addition of C(1)-ammonium enolates to pyridinium salts

et al. 2021

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“…It is worth noting that this procedure can be also used to prepare chiral N-phenyl pyrroles 16c (Scheme 10). The chiral center introduced in the starting N-carbamoyl-1,2-dihydropyridine 22 is maintained through the synthesis of both the corresponding arylnitroso NDA bicycle and pyrrole adduct [37]. This catalytic asymmetric arylation of pyridine devised by Doyle can be considered as a reliable entry to non-racemic 1,2-dihydropyridines used as starting material at the couple stage.…”

Section: Scheme 6 Synthesis Of Iminosugar Derivatives By Streithmentioning

confidence: 99%

Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity

2020

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This review focuses upon the use of nitroso Diels–Alder reactions as a structural complexity generating reaction that has been so far a quite scarcely treated topic, despite its potential. In particular, the use of N-acyl-1,2-dihydropyridines as a non-symmetrical diene component in nitroso Diels–Alder reactions encompasses an initial diversification of pathways giving rise to different cycloadducts (direct and inverse). Selective elaborations of these cycloadducts, basically using a reagent-based approach, deliver a discrete number of structurally diverse compounds, including some original heterobicyclic scaffolds and functionalized heterocycles. This forward synthetic planning allowed the individuation of a new biologically active compound based on a novel oxadiaza-bicyclic-[3.3.1]-nonene scaffold which is still under preclinical evaluation.

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“…However, substitution on the pyridine ring was not explored. Doyle's group, on the other hand, relied on nickel catalysis when dealing with arylzinc as nucleophiles [29,30]. 4-Methoxypyridine and C-4 unsubstituted pyridines were productively dearomatized, after activation with chloroformates, under differently optimized reaction conditions (Scheme 8).…”

Section: Scheme 2 Dearomatization Of Pyridine With An Organocalcium mentioning

confidence: 99%

Nucleophilic Dearomatization of Activated Pyridines

2018

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Amongst nitrogen heterocycles of different ring sizes and oxidation statuses, dihydropyridines (DHP) occupy a prominent role due to their synthetic versatility and occurrence in medicinally relevant compounds. One of the most straightforward synthetic approaches to polysubstituted DHP derivatives is provided by nucleophilic dearomatization of readily assembled pyridines. In this article, we collect and summarize nucleophilic dearomatization reactions of - pyridines reported in the literature between 2010 and mid-2018, complementing and updating previous reviews published in the early 2010s dedicated to various aspects of pyridine chemistry. Since functionalization of the pyridine nitrogen, rendering a (transient) pyridinium ion, is usually required to render the pyridine nucleus sufficiently electrophilic to suffer the attack of a nucleophile, the material is organized according to the type of N-functionalization. A variety of nucleophilic species (organometallic reagents, enolates, heteroaromatics, umpoled aldehydes) can be productively engaged in pyridine dearomatization reactions, including catalytic asymmetric implementations, providing useful and efficient synthetic platforms to (enantioenriched) DHPs. Conversely, pyridine nitrogen functionalization can also lead to pyridinium ylides. These dipolar species can undergo a variety of dipolar cycloaddition reactions with electron-poor dipolarophiles, affording polycyclic frameworks and embedding a DHP moiety in their structures.

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Nickel-catalyzed enantioselective arylation of pyridine

Cited by 73 publications

References 44 publications

Catalytic enantioselective synthesis of 1,4-dihydropyridines via the addition of C(1)-ammonium enolates to pyridinium salts

Catalytic enantioselective synthesis of 1,4-dihydropyridines via the addition of C(1)-ammonium enolates to pyridinium salts

Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity

Nucleophilic Dearomatization of Activated Pyridines

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