Department of Chemistry, College of Sciences, NC State University , Raleigh, North Carolina 27695, United States.
J Org Chem. 2018 Jan 5;83(1):12-22. doi: 10.1021/acs.joc.7b02299. Epub 2017 Oct 24.
An efficient synthesis of S-allyl thioimidate hydrobromide salts via coupling of thioamides with allyl bromide derivatives is described. A range of mono-, di-, and trisubstituted olefins as well as alkyl- and arylthioamides with variations in electronics are tolerated. A rapid anti-diastereoselective halocyclization of these salts provides a variety of substituted alkyl- and arylthiazolines. Initial development of an efficient enantioselective synthesis of quaternary-substituted thiazolines through the organo-catalyzed halocyclization of sulfonate thioimidate salts is also described.
通过硫代酰胺与烯丙基溴衍生物的偶联，描述了 S-烯丙基硫代脒氢溴酸盐盐的有效合成。该反应具有广泛的底物适用性，包括单取代、二取代和三取代烯烃，以及电子性质各异的烷基和芳基硫代酰胺。这些盐的快速反非对映选择性卤环化提供了各种取代的烷基和芳基噻唑啉。通过磺酸酯硫代脒盐的有机催化卤环化，初步开发了一种高效对映选择性合成季取代噻唑啉的方法。
