Issue 19, 2024
From the journal:

Organic Chemistry Frontiers

Unveiling the role of Lewis bases in cascade furan Diels–Alder cycloadditions: asymmetric synthesis of polycyclic quinazolinones†

Yuhan Li,a   Dongyi Zhang,a   Zhonglin Wei,b   Zhuoqi Zhang,a   Jinbao Xiang ORCID logo *a  and  Lianyou Zheng ORCID logo *a  

* Corresponding authors

a The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun, Jilin 130021, P. R. China
E-mail: lianyouzh@jlu.edu.cn, jbxiang@jlu.edu.cn

b College of Chemistry, Jilin University, Changchun 130012, P. R. China

Abstract

A Lewis base catalyzed asymmetric cascade reaction of 2-(furan-2-yl)quinazolinones with MBH carbonates was described. A variety of polycyclic quinazolinones containing four stereogenic centers were synthesized with up to 99% yield, 99% ee, and >20 : 1 dr. Control experiments revealed the key role of the Lewis base in promoting and stereo-controlling the IMDAF process.

Graphical abstract: Unveiling the role of Lewis bases in cascade furan Diels–Alder cycloadditions: asymmetric synthesis of polycyclic quinazolinones

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Article information

DOI
https://doi.org/10.1039/D4QO01114G
Article type
Research Article
Submitted
18 Jun 2024
Accepted
12 Aug 2024
First published
14 Aug 2024

Org. Chem. Front., 2024,11, 5488-5494

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Unveiling the role of Lewis bases in cascade furan Diels–Alder cycloadditions: asymmetric synthesis of polycyclic quinazolinones

Y. Li, D. Zhang, Z. Wei, Z. Zhang, J. Xiang and L. Zheng, Org. Chem. Front., 2024, 11, 5488 DOI: 10.1039/D4QO01114G

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