Lending a hand to asymmetric trifluoromethylthiolation:enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides

• 来源期刊: 中国科学:化学（英文版）
• 年，卷（期）: 2017,（12）
• 页码范围: 1565-1566
• 页数: 2页
• 语种: 英文
• DOI: 10.1007/s11426-017-9113-5

摘要

The introduction of a trifluoromethanesulfenyl group (SCF3)into organic molecules can,in principle,significantly enhance the cell-membrane permeability,metabolic stability and bioavailability because of its high lipophilicity and intrinsic electron-withdrawing properties.As a consequence,tremendous efforts have been made to develop diverse trifluoromethylthiolation protocols by using either electrophilic or nucleophilic trifluoromethylthiolating reagents.Though great success has been achieved in non-asymmetric trifluoromethylthiolation reactions,the asymmetric versions of these transformations remain a formidable challenge.So far,only sporadic examples of asymmetric installation of SCF3 have been demonstrated whereby the substrates were,however,mainly limited to β-ketoesters and oxindoles.Therefore,conceptually-novel strategies for asymmetric trifluoromethylthiolation of broader scopes of substrates are still a long-sought goal in the fields of synthetic and fluorine chemistry.