Issue 23, 2019
From the journal:

Organic & Biomolecular Chemistry

Iron-catalyzed domino Knoevenagel-hetero-Diels–Alder reaction: facile access to oxabicyclo[3.3.1]nonene derivatives†

Mingchang Wu,a   Junhang Yang,a   Fang Luo, ORCID logo *a   Cungui Cheng*a  and  Gangguo Zhu ORCID logo a  

* Corresponding authors

a Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China
E-mail: ccg@zjnu.cn, luofang19@zjnu.edu.cn

Abstract

A Fe-catalyzed domino Knoevenagel-hetero-Diels–Alder reaction of alkenyl aldehydes and 1,3-diketones has been developed. It provides straightforward access to a series of oxabicyclo[3.3.1]nonene derivatives in promising yields with excellent diastereoselectivity and functional group tolerance. The resultant bridged dihydropyrans can be smoothly converted into chromene derivatives, thus highlighting the synthetic utility of this method.

Graphical abstract: Iron-catalyzed domino Knoevenagel-hetero-Diels–Alder reaction: facile access to oxabicyclo[3.3.1]nonene derivatives

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Article information

DOI
https://doi.org/10.1039/C9OB00836E
Article type
Communication
Submitted
11 Apr 2019
Accepted
16 May 2019
First published
20 May 2019

Org. Biomol. Chem., 2019,17, 5684-5687

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Iron-catalyzed domino Knoevenagel-hetero-Diels–Alder reaction: facile access to oxabicyclo[3.3.1]nonene derivatives

M. Wu, J. Yang, F. Luo, C. Cheng and G. Zhu, Org. Biomol. Chem., 2019, 17, 5684 DOI: 10.1039/C9OB00836E

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