Wu Yichen, Qian Hao-Yang, Zhang Heng, Zou Jian-Ye, Wu Qing-Yan, Nie Xiao-Xue, Zheng Long, Peng Qian, Wang Peng
State Key Laboratory of Organometallic Chemistry and Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences CAS 345 Lingling Road Shanghai 200032 P. R. China
State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Tianjin Key Laboratory of Biosensing and Molecular Recognition, College of Chemistry, Nankai University Tianjin 300071 P. R. China
Chem Sci. 2025 Jun 5;16(27):12594-12602. doi: 10.1039/d5sc02711j. eCollection 2025 Jul 10.
Here, we report a highly efficient rhodium-catalysed enantioselective hydrosilylation of unactivated alkenes, achieving excellent regioselectivity and high enantioselectivity. The use of a commercially available chiral ferrocene-based phosphine-oxazoline ligand was crucial in achieving excellent chiral induction and high reactivity with undirected unactiviated alkenes, delivering Si-stereogenic monohydrosilanes in high yields and excellent enantioselectivities. This protocol represents a robust, scalable method for the enantioselective synthesis of Si-stereogenic monohydrosilanes, featuring a low catalyst loading, a broad substrate scope and exceptional functional group and heterocycle tolerance. Moreover, the late-stage functionalization of complex motifs opens a new avenue for incorporating chiral silicon motifs into pharmaceuticals and bioactive compounds.
在此，我们报道了一种高效的铑催化未活化烯烃的对映选择性硅氢化反应，实现了优异的区域选择性和高对映选择性。使用市售的基于手性二茂铁的膦-恶唑啉配体对于实现出色的手性诱导以及与无导向未活化烯烃的高反应性至关重要，能够以高收率和优异的对映选择性得到硅立体中心的单氢硅烷。该方法代表了一种用于对映选择性合成硅立体中心单氢硅烷的稳健、可扩展的方法，具有低催化剂负载量、广泛的底物范围以及对官能团和杂环的出色耐受性。此外，复杂结构的后期官能化开辟了一条将手性硅基序引入药物和生物活性化合物的新途径。
