Issue 14, 2021
From the journal:

Chemical Communications

Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds†

Hui-Chun Wu,a   Chen Wang,a   Ying-Han Chena  and  Yan-Kai Liu ORCID logo *ab  

* Corresponding authors

a Molecular Synthesis Center & Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China
E-mail: liuyankai@ouc.edu.cn

b Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, China

Abstract

An organocatalytic vinylogous Michael addition triggered triple-cascade reaction has been developed. 2-Hydroxycinnamaldehydes worked under iminium activation with either acyclic or cyclic ketone-derived α,α-dicyanoalkenes, yielding the benzofused oxabicyclo[3.3.1]nonanes bearing one quaternary stereocenter with excellent stereoselectivities.

Graphical abstract: Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds

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Article information

DOI
https://doi.org/10.1039/D0CC07761E
Article type
Communication
Submitted
26 Nov 2020
Accepted
07 Jan 2021
First published
08 Jan 2021

Chem. Commun., 2021,57, 1762-1765

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Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds

H. Wu, C. Wang, Y. Chen and Y. Liu, Chem. Commun., 2021, 57, 1762 DOI: 10.1039/D0CC07761E

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