Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring-Opening of 1,1-Biscyclopropyl Methanol Derivatives

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2022)

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Abstract
The diastereoselective double carbometalation reaction of cyclopropenes provides, in a single-pot operation, two omega-ene-[1,1]-bicyclopropyl ester derivatives. One regioisomer then undergoes a Pd-catalyzed addition of aryl iodide to provide skipped dienes possessing several distant stereocenters including two congested quaternary carbon centers with excellent diastereoselectivity.
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Key words
Bicyclopropyl Methanol, Carbometallalation, Cyclopropenes, Heck Addition, Quaternary Carbon Stereocenters
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