Copper-Catalyzed Desymmetrization of Prochiral Silanediols to Silicon-Stereogenic Silanols

作者：Jihui Gao, Pei-Lin Mai, Yicong Ge, Wei Yuan, Yingzi Li, Chuan He · 发表于：ACS Catalysis · 年份：2022 · DOI：10.1021/acscatal.2c02482 · 被引用次数：61 · 研究领域：Organoboron and organosilicon chemistry、Synthetic Organic Chemistry Methods、Synthesis and characterization of novel inorganic/organometallic compounds

Despite the growing demand for the enantioenriched silicon-stereogenic silanols in materials science, medicinal chemistry, and modern synthetic chemistry, the catalytic asymmetric synthesis of which remains a considerable challenge compared with their carbinol analogues. Herein, a copper-catalyzed desymmetrization of silanediols for the synthesis of various functionalized chiral silanols is demonstrated. The reaction features high atom economy, decent yield with excellent stereoselectivity, and H 2 as the sole byproduct. Key to the success for discrimination of the gem-diol groups in silanediol relies on an enantioselective σ-bond metathesis process. Further straightforward elaboration of the enantioenriched silicon-stereogenic silanols delivers several interesting chiral silane scaffolds without the loss of enantiopurities.