马尔科夫尼科夫法则
化学
立体选择性
溶剂分解
药物化学
亲核细胞
氧离子
炔烃
丁基锂
亲核加成
选择性
有机化学
离子
区域选择性
催化作用
水解
作者
Tarun Kumar Dinda,Syed Ramizul Kabir,Prasenjit Mal
标识
DOI:10.1021/acs.joc.3c00911
摘要
The stereoselective synthesis of Z-anti-Markovnikov styryl sulfides via an anionic thiolate–alkyne addition reaction was achieved when the terminal alkynes and benzyl mercaptans were reacted using tBuOLi (0.5 equiv) in EtOH under ambient conditions. Exclusive stereoselectivity (ca. 100%) was achieved by stereoelectronic control via anti-periplanar and anti-Markovnikov addition of benzylthiolates to phenylacetylenes. Solvolysis of lithium thiolate ion pairs in ethanol significantly suppresses the competing formation of the E-isomer. A remarkable enhancement of the Z-selectivity under a longer reaction time was observed.
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