Yang Gao-Feng, Yuan Yi, Tian Yin, Zhang Shi-Qi, Cui Xin, Xia Bing, Li Guang-Xun, Tang Zhuo
Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science, Chengdu, Sichuan 610041, China.
State Key Laboratory of Southwestern Chinese Medicine Resources, The Ministry of Education Key Laboratory of Standardization of Chinese Herbal Medicine, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China.
J Am Chem Soc. 2023 Mar 8;145(9):5439-5446. doi: 10.1021/jacs.2c13758. Epub 2023 Feb 22.
Direct construction of chiral S(VI) from prochiral S(II) is a formidable challenge due to the inevitable formation of stable chiral S(IV). Previous synthetic strategies rely on the conversion of chiral S(IV) or enantioselective desymmetrization of preformed symmetrical S(VI) substrates. Here, we report desymmetrizing enantioselective hydrolysis of in situ-generated symmetric aza-dichlorosulfonium from sulfenamides for the preparation of chiral sulfonimidoyl chlorides, which could be used as a general stable synthon for obtaining a series of chiral S(VI) derivatives.
从手性前体S(II)直接构建手性S(VI)是一项艰巨的挑战，因为不可避免地会形成稳定的手性S(IV)。以前的合成策略依赖于手性S(IV)的转化或预制对称S(VI)底物的对映选择性去对称化。在此，我们报道了从亚磺酰胺原位生成的对称氮杂二氯锍的对映选择性去对称水解反应，用于制备手性磺酰亚胺酰氯，其可作为一种通用的稳定合成子来获得一系列手性S(VI)衍生物。
