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A dienamine-mediated deconjugative addition/cyclization cascade of γ,γ-disubstituted enals with carboxylic acid-activated enones: a rapid access to highly functionalized γ-lactones

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An aminocatalytic deconjugative addition/cyclization cascade of γ,γ-disubstituted enals with carboxylic acid-activated enones was realized. The in situ generated dienamine species was regioselectively trapped at the α position by carboxylic acid-activated… Click to show full abstract

An aminocatalytic deconjugative addition/cyclization cascade of γ,γ-disubstituted enals with carboxylic acid-activated enones was realized. The in situ generated dienamine species was regioselectively trapped at the α position by carboxylic acid-activated enones, leading to highly functionalized γ-lactones with excellent enantioselectivities. Further synthetic elaboration of the products allows diverse synthesis of a set of complex chiral targets.

Keywords: activated enones; cyclization cascade; carboxylic acid; acid activated; addition cyclization; deconjugative addition

Journal Title: Organic chemistry frontiers
Year Published: 2020

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