Cooperative Chiral Lewis Base/Palladium‐Catalyzed Asymmetric Syntheses of Methylene‐Containing δ‐Lactams

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Abstract: We herein report a two‐step approach for the enantioselective synthesis of novel chiral δ‐lactams. By using a cooperative chiral ITU/achiral Pd‐catalyst system, this protocol proceeds via an asymmetric α‐allylation of activated aryl esters first, followed by an acid‐mediated lactam formation. A variety of differently substituted products could be obtained with usually high levels of enantioselectivities and in reasonable yields (16 examples, up to 98: 2 er and 73 % yield over two steps). In addition, further utilizations of the products via transformations of the exocyclic double bond were successfully carried out as well.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Cooperative Chiral Lewis Base/Palladium‐Catalyzed Asymmetric Syntheses of Methylene‐Containing δ‐Lactams ; day:09 ; month:11 ; year:2023 ; extent:6
European journal of organic chemistry ; (09.11.2023) (gesamt 6)

Creator: Zebrowski, Paul
Monkowius, Uwe
Waser, Mario

DOI: 10.1002/ejoc.202300982

URN: urn:nbn:de:101:1-2023111014050829473150

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 10:50 AM CEST

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Zebrowski, Paul
Monkowius, Uwe
Waser, Mario

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Cooperative Chiral Lewis Base/Palladium‐Catalyzed Asymmetric Syntheses of Methylene‐Containing δ‐Lactams

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Other Objects (12)

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Palladium-Catalyzed Carbonylative Cycloaddition of Acylsilanes and Imines to Access β-Lactams

Catalytic Access to Chiral δ ‐Lactams via Nucleophilic Dearomatization of Pyridine Derivatives

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Biocatalytic production of bicyclic β-lactams with three contiguous chiral centres using engineered crotonases

Desymmetrization of prochiral cyclobutanones via nitrogen insertion : a concise route to chiral γ-lactams

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Biocatalytic, Enantioselective Synthesis of Lactams

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Palladium-Catalyzed Carbonylative Cycloaddition of Acylsilanes and Imines to Access β-Lactams

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Direct Access to α,β‐Unsaturated γ‐Lactams via Palladium‐Catalysed Carbonylation of Propargylic Ureas.

Biocatalytic, Enantioselective Synthesis of Lactams

Enantioselective Synthesis of Sterically Hindered α‐Allyl‐α‐Aryl Lactams via Palladium‐Catalysed Decarboxylative Asymmetric Allylic Alkylation

Chiral γ-Lactams by Enantioselective Cyclopropane Functionalization

Bifurcated synthesis of methylene-lactone- and methylene-lactam-fused spirolactams via electrophilic amide allylation of γ-phenylthio-functionalized γ-lactams

Palladium-Catalyzed Carbonylative Cycloaddition of Acylsilanes and Imines to Access β-Lactams

Catalytic Access to Chiral δ ‐Lactams via Nucleophilic Dearomatization of Pyridine Derivatives

Catalytic Access to Chiral δ ‐Lactams via Nucleophilic Dearomatization of Pyridine Derivatives

Biocatalytic production of bicyclic β-lactams with three contiguous chiral centres using engineered crotonases

Desymmetrization of prochiral cyclobutanones via nitrogen insertion : a concise route to chiral γ-lactams

Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ‐Lactams

(2+2) Cycloadditions of Methylene exo ‐Glycals: Synthesis of Glycopyranosylidene‐Spiro‐Azetidine‐2‐ones (β‐Lactams) and Cyclobutanones

Direct Access to α,β‐Unsaturated γ‐Lactams via Palladium‐Catalysed Carbonylation of Propargylic Ureas.

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