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Diastereoselective and Enantioselective Silylation of 2‑Arylcyclohexanols

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journal contribution
posted on 15.05.2015, 00:00 by Li Wang, Ravish K. Akhani, Sheryl L. Wiskur
The silylation-based kinetic resolution of trans 2-arylcyclohexanols was accomplished by employing a triaryl silyl chloride as the derivatizing reagent with a commercially available isothiourea catalyst. The methodology is selective for the trans diastereomer over the cis, which provides an opportunity to selectively derivatize one stereoisomer out of a mixture of four. By employing this technology, a facile, convenient method to form a highly enantiomerically enriched silylated alcohol was accomplished through a one-pot reduction–silylation sequence that started with a 2-aryl-substituted ketone.