Synthesis of β‐Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N‐Allylation of Halogenated Amides with Morita‐Baylis‐Hillman Carbonates

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Abstract: Trifluoro‐ and trichloroacetamides serving as pronucleophiles undergo enantioselective Lewis base catalyzed N‐allylation with Morita‐Baylis‐Hillman carbonates to produce enantioenriched β‐amino acid derivatives. The reactions proceed as a kinetic resolution to give the allylation products and the remaining carbonates in good yields and high enantioselectivity. The obtained products are amenable to diastereoselective derivatization to produce a library of spiro‐isoxazoline lactams.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Synthesis of β‐Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N‐Allylation of Halogenated Amides with Morita‐Baylis‐Hillman Carbonates ; day:16 ; month:01 ; year:2024 ; extent:8
Chemistry - a European journal ; (16.01.2024) (gesamt 8)

Creator: Nosovska, Olena
Liebing, Phil
Vilotijević, Ivan

DOI: 10.1002/chem.202304014

URN: urn:nbn:de:101:1-2024011714040809596996

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

Last update: 15.08.2025, 7:34 AM CEST

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Other Objects (12)

Synthesis of β‐Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N‐Allylation of Halogenated Amides with Morita‐Baylis‐Hillman Carbonates

Synthesis of β‐Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N‐Allylation of Halogenated Amides with Morita‐Baylis‐Hillman Carbonates

The Morita–Baylis–Hillman Reaction

The Morita–Baylis–Hillman Reaction

Et3B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita–Baylis–Hillman alcohols

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Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

Organocatalyzed Morita-Baylis-Hillman reaction : mechanism and catalysis

Hochschulschrift

Organocatalyzed Morita-Baylis-Hillman reaction : mechanism and catalysis

Palladium-Catalyzed Enantioselective Aza-Morita–Baylis–Hillman Reaction

Palladium-Catalyzed Enantioselective Aza-Morita–Baylis–Hillman Reaction

Engineered Biocatalyst Permits Enantioselective Morita–Baylis–Hillman Reaction

Engineered Biocatalyst Permits Enantioselective Morita–Baylis–Hillman Reaction

Morita–Baylis–Hillman reaction of acrylamide with isatin derivatives

Morita–Baylis–Hillman reaction of acrylamide with isatin derivatives

Direct C(sp3)–H allylation of 2-alkylpyridines with Morita–Baylis–Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement

Direct C(sp3)–H allylation of 2-alkylpyridines with Morita–Baylis–Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement

Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction

Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction

Synthesis of β‐Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N‐Allylation of Halogenated Amides with Morita‐Baylis‐Hillman Carbonates

Synthesis of β‐Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N‐Allylation of Halogenated Amides with Morita‐Baylis‐Hillman Carbonates

The Morita–Baylis–Hillman Reaction

The Morita–Baylis–Hillman Reaction

Et3B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita–Baylis–Hillman alcohols

Et3B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita–Baylis–Hillman alcohols

Aza-Morita–Baylis–Hillman Synthesis of Benzoxazepines

Aza-Morita–Baylis–Hillman Synthesis of Benzoxazepines

Benzonaphthyridines from Morita-Baylis-Hillman Adduct Acetates

Benzonaphthyridines from Morita-Baylis-Hillman Adduct Acetates

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

Organocatalyzed Morita-Baylis-Hillman reaction : mechanism and catalysis

Hochschulschrift

Organocatalyzed Morita-Baylis-Hillman reaction : mechanism and catalysis

Palladium-Catalyzed Enantioselective Aza-Morita–Baylis–Hillman Reaction

Palladium-Catalyzed Enantioselective Aza-Morita–Baylis–Hillman Reaction

Engineered Biocatalyst Permits Enantioselective Morita–Baylis–Hillman Reaction

Engineered Biocatalyst Permits Enantioselective Morita–Baylis–Hillman Reaction

Morita–Baylis–Hillman reaction of acrylamide with isatin derivatives

Morita–Baylis–Hillman reaction of acrylamide with isatin derivatives

Direct C(sp3)–H allylation of 2-alkylpyridines with Morita–Baylis–Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement

Direct C(sp3)–H allylation of 2-alkylpyridines with Morita–Baylis–Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement

Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction

Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction

Synthesis of β‐Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N‐Allylation of Halogenated Amides with Morita‐Baylis‐Hillman Carbonates

Synthesis of β‐Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N‐Allylation of Halogenated Amides with Morita‐Baylis‐Hillman Carbonates

The Morita–Baylis–Hillman Reaction

The Morita–Baylis–Hillman Reaction

Et3B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita–Baylis–Hillman alcohols

Et3B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita–Baylis–Hillman alcohols

Aza-Morita–Baylis–Hillman Synthesis of Benzoxazepines

Aza-Morita–Baylis–Hillman Synthesis of Benzoxazepines

Benzonaphthyridines from Morita-Baylis-Hillman Adduct Acetates

Benzonaphthyridines from Morita-Baylis-Hillman Adduct Acetates

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

Organocatalyzed Morita-Baylis-Hillman reaction : mechanism and catalysis

Hochschulschrift

Organocatalyzed Morita-Baylis-Hillman reaction : mechanism and catalysis

Palladium-Catalyzed Enantioselective Aza-Morita–Baylis–Hillman Reaction

Palladium-Catalyzed Enantioselective Aza-Morita–Baylis–Hillman Reaction

Engineered Biocatalyst Permits Enantioselective Morita–Baylis–Hillman Reaction

Engineered Biocatalyst Permits Enantioselective Morita–Baylis–Hillman Reaction

Morita–Baylis–Hillman reaction of acrylamide with isatin derivatives

Morita–Baylis–Hillman reaction of acrylamide with isatin derivatives

Direct C(sp3)–H allylation of 2-alkylpyridines with Morita–Baylis–Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement

Direct C(sp3)–H allylation of 2-alkylpyridines with Morita–Baylis–Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement

Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction

Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction

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