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Merging singlet-oxygen induced furan oxidations with organocatalysis: synthesis of enantiopure cyclopentanones and hydrindanes

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Abstract

A new methodology is described herein which converts simple and readily accesible furan substrates into complex enantio-enriched carbocyclic skeletons through the implementation of a simple one-pot procedure. Singlet oxygen furan photoxygenation affords an enedione which then participates in an organocatalysed double-Michael reaction with an enal to furnish a cyclopentanone structure with up to four new contiguous stereogenic centres. The enantioselectivity and diastereoselectivity of this process are both excellent. If desired, further aldol-annulation steps can be appended to the cascade reaction sequence to afford key enantiopure hydrindane motifs.

Graphical abstract: Merging singlet-oxygen induced furan oxidations with organocatalysis: synthesis of enantiopure cyclopentanones and hydrindanes

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Article information


Submitted
04 Mar 2020
Accepted
24 Mar 2020
First published
24 Mar 2020

This article is Open Access

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Merging singlet-oxygen induced furan oxidations with organocatalysis: synthesis of enantiopure cyclopentanones and hydrindanes

D. Kalaitzakis, M. Sofiadis, V. Tsopanakis, T. Montagnon and G. Vassilikogiannakis, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00468E

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