<br/>Enantioenriched chiral-at-silicon compounds have been studied as chiral auxiliaries, resolving agents, and as drug candidates. Chiral silicon compounds offer unique reactivities and physical properties that are not available for carbon chemistry and are thus of great interest. There are currently limited methods for the synthesis of enantioenriched silicon centers. In this work, we report the enantioselective synthesis of bifunctional stereogenic-at-silicon compounds via silylation of a prochiral silanediol. The method produces excellent yields and enantioselectivity up to 98:2 using a chiral amide catalyst. This desymmetrization process can be applied to several silanediol and silyl electrophiles as substrates. Co-crystallization and X-ray studies reveal insight into the binding interactions of the catalyst and silanediol substrate, which is further supported by <sup>1</sup>H NMR binding studies.

Catalytic enantioselective synthesis of siloxanols from prochiral silanediols

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ACS Fall 2022

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