Issue 3, 2020
From the journal:

Organic Chemistry Frontiers

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†

Wei Jiang,ac   Jia Zhou,c   Ai-Jun Ma,a   Dongli Li, ORCID logo a   Yan-Yan Ma,a   Deng-Gao Zhao,a   Si-Hua Hou,c   Jun-Bing Lin*bc  and  Shu-Yu Zhang ORCID logo *ac  

* Corresponding authors

a School of Biotechnology and Health Sciences, International Healthcare Innovation Institute, Wuyi University, Jiangmen 529020, China

b Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an 716000, China

c Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China
E-mail: linjunbing@sjtu.edu.cn, zhangsy16@sjtu.edu.cn

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

DOI
https://doi.org/10.1039/C9QO01367A
Article type
Research Article
Submitted
12 Nov 2019
Accepted
27 Dec 2019
First published
30 Dec 2019

Org. Chem. Front., 2020,7, 571-577

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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

W. Jiang, J. Zhou, A. Ma, D. Li, Y. Ma, D. Zhao, S. Hou, J. Lin and S. Zhang, Org. Chem. Front., 2020, 7, 571 DOI: 10.1039/C9QO01367A

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