Luo Hui-Yun, Xie Yu-Yang, Song Xu-Feng, Dong Jia-Wei, Zhu Deng, Chen Zhi-Min
School of Chemistry and Chemical Engineering & Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
Chem Commun (Camb). 2019 Aug 14;55(63):9367-9370. doi: 10.1039/c9cc04758a. Epub 2019 Jul 18.
An efficient method for the preparation of chiral sulfenylated lactones has been described based on Lewis base-catalyzed enantioselective sulfenylation of unsaturated carboxylic acids. The scope of this method includes two enantioselective cyclization reactions: 5-endo and 6-exo thiolactonizations of alkenes. Two types of lactones were obtained with up to 95% ee and 99% yield. Additionally, this methodology has been applied in the formal syntheses of bioactive natural products (-)-nicotlactone B and (-)-galbacin.
基于路易斯碱催化的不饱和羧酸对映选择性亚磺酰化反应，已经描述了一种制备手性亚磺酰化内酯的有效方法。该方法的适用范围包括两种对映选择性环化反应：烯烃的5-内型和6-外型硫代内酯化反应。得到了两种内酯，对映体过量率高达95%，产率高达99%。此外，该方法已应用于生物活性天然产物（-）-烟曲霉内酯B和（-）-加巴辛的形式合成中。
