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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

AuthorsAlcaide, Benito ; Almendros, Pedro ; Aragoncillo, Cristina; Callejo, Ricardo; Ruiz, M. Pilar
Issue Date2013
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 78: 10154- 10165 (2013)
AbstractThe 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. © 2013 American Chemical Society.
Identifiersdoi: 10.1021/jo4015358
issn: 0022-3263
e-issn: 1520-6904
Appears in Collections:(IQOG) Artículos
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