Oxidative DMSO Cyclization Cascade to Bicyclic Hydroxyketonitriles.

J Org Chem

Department of Chemistry, Drexel University, 3401 Chestnut Street Philadelphia, Pennsylvania 19104, United States.

Published: May 2022

Thermolysis of ω-iodoalkyl-β-siloxyalkenenitriles in DMSO triggers an oxidative cyclization cascade that affords highly oxygenated hydrindanones, decalones, and undecanones. The cyclization cascade is highly unusual on three counts: the cyclization installs a contiguous array of tertiary-quaternary-tertiary centers, thermolysis equilibrates a quaternary center, and the enolsilyl ether crossed-aldol proceeds without a catalyst.

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http://dx.doi.org/10.1021/acs.joc.2c00364DOI Listing

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