Diastereoselective and Enantioselective Silylation of 2-Arylcyclohexanols

作者:Wang Li; Akhani Ravish K; Wiskur Sheryl L*
来源:Organic Letters, 2015, 17(10): 2408-2411.
DOI:10.1021/acs.orglett.5b00919

摘要

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.

  • 出版日期2015-5-15