Issue 23, 2019

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

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

Supplementary files

Article information

Article type
Communication
Submitted
11 Apr 2019
Accepted
16 May 2019
First published
20 May 2019

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

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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