Ring Forming Approaches to para-Quinones: Toward a General Diels–Alder Disconnection

Abstract

para-Quinones feature extensively as targets and/or intermediates throughout a number of chemical and biological subdisciplines, highlighting the importance of efficient preparative methods. This Synpacts article provides an overview of ring forming approaches to para-hydroquinones and para-benzoquinones, concluding with our recent contribution concerning the development of 2,5-bis(tert-butyldimethylsilyloxy)furans as vicinal bisketene equivalents in the Diels–Alder reaction.

1 Introduction

2 Ring Forming Approaches to para-Quinones

2.1 Hauser–Kraus Annulation

2.2 Moore–Liebeskind Rearrangement

2.3 Wulff–Dötz Reaction

2.4 Oxidative Bergman Cyclization

2.5 Diels–Alder Strategies

2.5.1 Ketene–Enol Equivalents

2.5.2 Bisketene Equivalents

3 Toward an Improved Bisketene Equivalent

4 Conclusion

Key words

Diels–Alder - cycloaddition - annulation - hydroquinone - benzoquinone - furan

Publication History

Received: 17 February 2022

Accepted after revision: 28 February 2022

Article published online:
27 June 2022

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