Palladium‐Catalyzed Cascade to Benzoxepins by Using Vinyl‐Substituted Donor–Acceptor Cyclopropanes

Matteo Faltracco, Koen N. A. van de Vrande, Martijn Dijkstra, Jordy M. Saya, Trevor A. Hamlin, Eelco Ruijter

Angewandte Chemie International Edition · 2021 · 49 citations · 59 references

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Abstract

A palladium-catalyzed intermolecular cascade (4+3) cyclocondensation of salicylaldehydes and vinylcyclopropanes is reported. A key feature of the reaction is the use of a phosphonate group as an acceptor moiety on the cyclopropane, exploiting its propensity to undergo olefination with aldehydes. Subsequent O-allylation enabled the formation of a range of substituted benzoxepinsWith a novel chiral ligand, the products were obtained in generally good yield and with reasonable enantioselectivity.

References

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