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Published on: May 26, 2019
Isothiourea-Catalyzed Acylative Desymmetrization of Silicon-Centered Bisphenols
Xuanlong Liao1, Hongwei Zhou2, Xingkuan Chen3
1Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China.
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.
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