Preparative Organic Chemistry
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ChemInform Abstract: Synthesis of δ-Lactones from 2-Alkynyl Epoxides and 4-Alkynyl-1,3-dioxolan-2-ones by Palladium-Catalyzed Carbonylation and Conjugate Nucleophilic Addition.
First published: 30 May 2010
Abstract
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ChemInform Abstract
Palladium-catalyzed carbonylation of oxiranes (I) and (VII) and dioxolanes (XIII), (XVI), and (XIX) gives the corresponding allenes which undergo stereocontrolled tandem conjugate addition—cyclization with cuprate (V) to afford β,γ-unsaturated δ-lactones. Stereoselective reduction of allenes (IV) and (VIII) with NaBH4 results in the formation (E)-pentenoates (X) and (XII).
