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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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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.

Graphical abstract: 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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Article information


Submitted
12 Nov 2019
Accepted
27 Dec 2019
First published
30 Dec 2019

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

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

W. Jiang, J. Zhou, A. Ma, D. Li, Y. Ma, D. Zhao, S. Hou, J. Lin and S. Zhang, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01367A

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