Enantioconvergent Construction of Stereogenic Silicon Via Lewis Base-catalyzed Dynamic Kinetic Silyletherification of Racemic Chlorosilanes

Overview

Journal Nat Commun

Specialty Biology

Date 2023 Aug 14

PMID 37580365

Authors

Tianbao Hu

Chen Zhao

Yan Zhang

Yuzhong Kuang

Lu Gao

Wanshu Wang

Zhishan Su

Zhenlei Song

Affiliations

Soon will be listed here.

Abstract

Organosilanes possessing an enantioenriched stereogenic silicon center are important in many branches of chemistry, yet they remain challenging to synthesize in a practical and scalable way. Here we report a dynamic kinetic silyletherification process of racemic chlorosilanes with (S)-lactates using 4-aminopyridine as a Lewis base catalyst. This enantioconvergent approach asymmetrically constructs the stereogenic silicon center in a different manner from traditional resolution or desymmetrization. A range of silylethers have been prepared with high diastereoselectivity on up to 10 g-scale, allowing the practical synthesis of diverse enantioenriched organosilane analogs.

Citing Articles

Copper-catalyzed intermolecular Regio- and Enantioselective Hydrosilylation of Alkenes with Prochiral Silanes.

Zhu X, Gao W, Xu J, Wang Z, Zhao J, Xu Y Nat Commun. 2025; 16(1):378.

PMID: 39753543 PMC: 11698737. DOI: 10.1038/s41467-024-55592-1.

Carbon-silicon-switch effect in enantioselective construction of silicon-stereogenic center from silacyclohexadienones.

Yan Y, Wei Q, Su Z, Hang N, Hayashi T, Ming J Nat Commun. 2024; 15(1):9915.

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