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Tuning the Reactivity of Oxygen/Sulfur by Acidity of the Catalyst in Prins Cyclization: Oxa- versus Thia-Selectivity

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NIAID Data Ecosystem2026-03-08 收录
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https://figshare.com/articles/dataset/Tuning_the_Reactivity_of_Oxygen_Sulfur_by_Acidity_of_the_Catalyst_in_Prins_Cyclization_Oxa_versus_Thia_Selectivity/2312764
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资源简介:
An unprecedented oxa- versus thia-selectivity has been observed in Prins cyclization of 6-mercapto­hex-3-en-1-ol with aldehydes. In the presence of a stoichiometric amount of strong Lewis or Brønsted acids, the reaction provides the hexa­hydro-2H-thieno­[3,2-c]­pyran skeleton predominantly via oxonium-Prins cyclization. In contrast, a catalytic amount of weak Lewis or Brønsted acids provides the hexa­hydro-2H-thio­pyrano­[4,3-b]­furan preferentially through thionium-Prins cyclization.
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2016-02-17
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