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Ring Expansion versus Cyclization in 4-Oxoazetidine-2- carbaldehydes Catalyzed by Molecular Iodine: Experimental and Theoretical Study in Concert

AuthorsAlcaide, Benito ; Almendros, Pedro ; Cabrero, Gema; Callejo, Ricardo; Ruiz, M. Pilar; Arnó, Manuel; Domingo, Luis R.
Reaction mechanisms
Issue DateJul-2010
CitationAdvanced Synthesis and Catalysis 352(10): 1688-1700 (2010)
AbstractMolecular iodine (10 mol%) efficiently catalyzes the ring expansion of 4-oxoazetidine-2-carbaldehydes in the presence of tert-butyldimethylsilyl cyanide, or allylic and propargylic trimethylsilanes to afford protected 5-functionalized-3,4-dihydroxypyrrolidin-2-ones with good yield and high diastereoselectivity, through a C3C4 bond cleavage of the β-lactam nucleus. Interestingly, in contrast to the iodine-catalyzed reactions of 3-alkoxy-β-lactam aldehydes which lead to the corresponding -lactam derivatives (rearrangement adducts), the reactions of 3-aryloxy-β-lactam aldehydes under similar conditions gave β-lactam-fused chromanes (cyclization adducts) as the sole products, through exclusive electrophilic aromatic substitution involving the C3 aromatic ring and the carbaldehyde. In order to support the mechanistic proposals, theoretical studies have been performed.
Description13 páginas, 3 figuras, 12 esquemas, 2 tablas.-- El documento en word es el articulo post-print.
Publisher version (URL)http://dx.doi.org/10.1002/adsc.201000171
Appears in Collections:(IQOG) Artículos
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