Organocatalyzed Three-Component Ugi and Passerini Reactions of 4‑Oxoazetidine-2-carbaldehydes and Azetidine-2,3-diones. Application to the Synthesis of γ‑Lactams and γ‑Lactones

Organocatalyzed Three-Component Ugi and Passerini Reactions of 4‑Oxoazetidine-2-carbaldehydes and Azetidine-2,3-diones. Application to the Synthesis of γ‑Lactams and γ‑Lactones

The organocatalyzed U-3CR of 4-oxoazetidine-2-carbaldehydes has been studied. In addition, the organocatalyzed P-3CR of 4-oxoazetidine-2-carbaldehydes and azetidine-2,3-diones has been described for the first time. U-3CR and P-3CR adducts have been obtained in good yields and reasonable diastereosel...

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Veröffentlicht in:Journal of organic chemistry 2013-10, Vol.78 (20), p.10154-10165
Hauptverfasser: Alcaide, Benito, Almendros, Pedro, Aragoncillo, Cristina, Callejo, Ricardo, Ruiz, M. Pilar
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container_end_page 10165
container_issue 20
container_start_page 10154
container_title Journal of organic chemistry
container_volume 78
creator Alcaide, Benito
Almendros, Pedro
Aragoncillo, Cristina
Callejo, Ricardo
Ruiz, M. Pilar
description The organocatalyzed U-3CR of 4-oxoazetidine-2-carbaldehydes has been studied. In addition, the organocatalyzed P-3CR of 4-oxoazetidine-2-carbaldehydes and azetidine-2,3-diones has been described for the first time. U-3CR and P-3CR adducts have been obtained in good yields and reasonable diastereoselectivities. Phenyl phosphinic acid has been the catalyst of choice to study the scope of both organocatalyzed multicomponent reactions using a variety of β-lactams, isocyanides, and amines. Highly functionalized U-3CR and P-3CR adducts derived from β-lactams have proved to be useful substrates for the preparation of enantiopure γ-lactams and γ-lactones via N1–C2 β-lactam ring opening/cyclization under acidic or basic conditions.
doi_str_mv 10.1021/jo4015358
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title Organocatalyzed Three-Component Ugi and Passerini Reactions of 4‑Oxoazetidine-2-carbaldehydes and Azetidine-2,3-diones. Application to the Synthesis of γ‑Lactams and γ‑Lactones
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