Published March 15, 2019 | Version v1
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Vinylogous Reactivity of Cyclic 2‐Enones: Organocatalysed Asymmetric Addition to 2‐Enals to Synthesize Fused Carbocycles

Description

A method for asymmetric and site selective annulations at the γ and γ′ positions of cyclic 2‐enones with α,β‐unsaturated aldehydes has been developed. The organocatalysed [3+3]‐annulations proceed with high levels of regio‐, diastereo‐, and enantioselectivity, affording a series of high value fused carbocycles. Further elaboration gave key lactones (both bridged and fused).

Notes

This is the accepted version of the following article: Angew. Chem. Int. Ed. 2019, 58, 6742 – 6746. , which has been published in final form at https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201901902. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy.

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Funding

European Commission
SINOXYGEN - Advancing the Green Chemistry of Singlet Oxygen and Applying it to Synthetic Challenges 277588