Isothiourea-Catalyzed Acylative Desymmetrization of Silicon-Centered Bisphenols
Xuanlong Liao, Hongwei Zhou, Xingkuan Chen, Jianfeng Xu
Abstract
The preparation of optically pure organosilicon compounds bearing a stereogenic center at the silicon atom is an attractive but challenging enterprise. Herein we disclose an isothiourea (ITU)-catalyzed monoacylation reaction of silicon-centered bisphenols with 2,2-diphenylacetic pivalic anhydride, delivering tetrasubstituted organosilanes in moderate to excellent yields (36-91%) with moderate to excellent enantiomeric ratios (68:32-97.5:2.5). This organocatalytic desymmetrization approach can be performed on gram scale, and the products can be converted to other valuable compounds.
Topics & Concepts
DesymmetrizationChemistryCatalysisSiliconCombinatorial chemistryOrganic chemistryStereochemistryMedicinal chemistryEnantioselective synthesisAsymmetric Synthesis and CatalysisOrganoboron and organosilicon chemistrySynthetic Organic Chemistry Methods