Hu Tianbao, Zhao Chen, Zhang Yan, Kuang Yuzhong, Gao Lu, Wang Wanshu, Su Zhishan, Song Zhenlei
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, 610041, Chengdu, China.
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, 610064, Chengdu, China.
Nat Commun. 2023 Aug 14;14(1):4900. doi: 10.1038/s41467-023-40558-6.
Organosilanes possessing an enantioenriched stereogenic silicon center are important in many branches of chemistry, yet they remain challenging to synthesize in a practical and scalable way. Here we report a dynamic kinetic silyletherification process of racemic chlorosilanes with (S)-lactates using 4-aminopyridine as a Lewis base catalyst. This enantioconvergent approach asymmetrically constructs the stereogenic silicon center in a different manner from traditional resolution or desymmetrization. A range of silylethers have been prepared with high diastereoselectivity on up to 10 g-scale, allowing the practical synthesis of diverse enantioenriched organosilane analogs.
具有对映体富集的手性硅中心的有机硅烷在许多化学分支中都很重要，但以实用且可扩展的方式合成它们仍然具有挑战性。在此，我们报道了使用4-氨基吡啶作为路易斯碱催化剂，外消旋氯硅烷与(S)-乳酸酯的动态动力学硅醚化过程。这种对映收敛方法以与传统拆分或去对称化不同的方式不对称地构建手性硅中心。已在高达10 g规模上以高非对映选择性制备了一系列硅醚，从而能够实际合成各种对映体富集的有机硅烷类似物。
