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Chirality transfer in the synthesis of 2,3-dihydro-1,4-dithiine derivatives
Synthetic Communications ( IF 1.8 ) Pub Date : 2020-08-08 , DOI: 10.1080/00397911.2020.1801746
Wojciech J. Depa 1 , Natalia Buszta 1 , Piotr A. Guńka 2 , Janusz Zachara 2 , Agata Bajek-Bil 1 , Grażyna Groszek 1
Affiliation  

Abstract A new method for the synthesis of chiral 2,3-dihydro-1,4-dithiine derivatives that involves a reaction of chiral cyclic aliphatic dithioacetal in the presence of Lewis acid has been developed. The title product contains a 1,4-dithiane substituent with two stereogenic centers. The presence of a stereogenic center in the α position to the cyclic dithioacetal substrate controls the stereogenicity of two centers in the newly formed molecule whose absolute configuration is defined. The mechanism based on chirality transfer process was proposed. Graphical Abstract

中文翻译:

2,3-dihydro-1,4-dithiine 衍生物合成中的手性转移

摘要 开发了一种合成手性 2,3-二氢-1,4-二硫氨酸衍生物的新方法,该方法涉及手性环状脂肪族二硫缩醛在路易斯酸存在下的反应。标题产品包含具有两个立体中心的 1,4-二噻烷取代基。在环状二硫缩醛底物的 α 位置存在立体中心控制着新形成的分子中两个中心的立体性,其绝对构型已定义。提出了基于手性转移过程的机理。图形概要
更新日期:2020-08-08
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