Chemoenzymatic Asymmetric Synthesis of Pyridine‐Based α‐Fluorinated Secondary Alcohols

Broese, Timo; Ehlers, Peter; Langer, Peter; Langermann, Jan von

doi:10.1002/cbic.202100392

Cited by 3 publications

(1 citation statement)

References 43 publications

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“…The authors have cited additional references within the Supporting Information. [20][21][22][23][24][25]…”

Section: Supporting Informationmentioning

confidence: 99%

Synthesis and Photochemical Characterization of Indolizine Fluorophores Obtained by a Multicomponent Palladium Iodide−Catalyzed Oxidative Aminocarbonylation Approach

Ziccarelli,

Amuso,

Mancuso

et al. 2024

Eur J Org Chem

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A catalytic carbonylative method for the direct, multicomponent synthesis of indolizine fluorophores has been developed. The process is based on the PdI2/KI‐catalyzed oxidative aminocarbonylation of 2‐(pyridin‐2‐yl)pent‐4‐yn‐1‐carbonyl compounds leading to the corresponding 2‐ynamide intermediates, followed in situ by 5‐exo‐dig cyclization (by amine‐promoted conjugate addition of the pyridine ring nitrogen) and aromatization, to give the finally isolated N,N‐disubstituted 2‐(indolizin‐3‐yl)acetamides. Reactions are carried out under relatively mild conditions (100 °C under 20 atm of a 4:1 mixture CO‒air for 6‐15 h) in MeCN as the solvent and with a low catalyst loading (0.33 mol% PdI2), in the presence of 0.5 equiv of KI and 3 equiv of a secondary amine. The optical properties of representative 2‐(indolizin‐3‐yl)acetamide products have also been investigated.

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“…The authors have cited additional references within the Supporting Information. [20][21][22][23][24][25]…”

Section: Supporting Informationmentioning

confidence: 99%

Synthesis and Photochemical Characterization of Indolizine Fluorophores Obtained by a Multicomponent Palladium Iodide−Catalyzed Oxidative Aminocarbonylation Approach

Ziccarelli,

Amuso,

Mancuso

et al. 2024

Eur J Org Chem

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Chemoenzymatic Asymmetric Synthesis of Pyridine‐Based α‐Fluorinated Secondary Alcohols

et al. 2021

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Dedicated to Professor Udo Kragl on the occasion of his 60th birthday.Fluoro-substituted and heteroaromatic compounds are valuable intermediates for a variety of applications in pharma-and agrochemistry and synthetic chemistry. This study investigates the chemoenzymatic preparation of chiral alcohols bearing a heteroaromatic ring with an increasing degree of fluorination in α-position. Starting from readily available picoline derivatives prochiral α-halogenated acyl moieties were introduced with excellent selectivity and 64-95 % yield. The formed carbonyl group was subsequently reduced to the corresponding alcohols using the alcohol dehydrogenase from Lactobacillus kefir, yielding an enantiomeric excess of 95-> 99 % and up to 98 % yield.

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Six-membered ring systems: pyridines and benzo derivatives

Badenock¹

2023

Progress in Heterocyclic Chemistry

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Chemoenzymatic Asymmetric Synthesis of Pyridine‐Based α‐Fluorinated Secondary Alcohols

Cited by 3 publications

References 43 publications

Synthesis and Photochemical Characterization of Indolizine Fluorophores Obtained by a Multicomponent Palladium Iodide−Catalyzed Oxidative Aminocarbonylation Approach

Synthesis and Photochemical Characterization of Indolizine Fluorophores Obtained by a Multicomponent Palladium Iodide−Catalyzed Oxidative Aminocarbonylation Approach

Chemoenzymatic Asymmetric Synthesis of Pyridine‐Based α‐Fluorinated Secondary Alcohols

Six-membered ring systems: pyridines and benzo derivatives

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