Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes

Catalytic asymmetric sulfenylation of double bonds has been achieved using a BINAM-based phosphoramide catalyst and an electrophilic sulfur source. Simple alkenes as well as styrenes afforded sulfenylated tetrahydrofurans and tetrahydropyrans by closure with pendant hydroxyl or carboxyl groups. Intermolecular thiofunctionalizations were also achieved with simple alcohols or carboxylic acids as the nucleophiles.

本研究采用基于联萘二胺的磷酰胺催化剂（BINAM-based phosphoramide catalyst）与亲电硫试剂（electrophilic sulfur source），成功实现了双键的催化不对称硫代化反应。简单烯烃与苯乙烯类底物可通过与自身悬挂的羟基或羧基发生环合反应，生成硫代化的四氢呋喃与四氢吡喃产物。此外，以简单醇或羧酸作为亲核试剂的分子间硫官能化反应同样得以实现。