Date

Tuesday 31 Mar 2026

Time

15:15 - 15:45

Location

BW008

Supervisor

Dmitri Filippov

Jury

Stefan van der Vorm

Silicon is a ubiquitous element in organic chemistry, where it is predominantly found as stationary phase in column chromatography (silica gel) and as a functional handle in protecting groups. It is also found in more niche applications, where silicon can be used as bioisosteres of carbon in medicinal chemistry. Similar to carbon, silicon atoms can be chiral when it bears four distinct substituents. The synthesis of such stereogenic silanes remains a rapidly evolving challenge. This work reviews two primary strategies for the synthesis of chiral silicon containing compounds: the construction of C-stereogenic silanes and Si-stereogenic silanes. First, the development of kinetic resolution (KR) of alcohols via selective silylation is discussed, with a primary focus on transition-metal catalysed methods. Utilizing Cu-H/chiral phosphine catalysis, this approach has been extended to resolve a diverse range of complex substrates, including tertiary propargylic alcohols, BINOL derivatives, and 1,3-diols. Second, recent breakthroughs in Si-stereogenic silanes are discussed. By employing strong and confined Brønsted acid catalysts, researchers were able to synthesize chiral silyl ethers from racemic methallyl-silanes or prochiral bis(methallyl)-silanes. Furthermore, both strategies were combined with dynamic methodologies and were able to break the 50% yield barrier from racemic mixtures to enantiopure compounds of regular KR. Together, these methodologies represent the current state of the art in stereogenic silane synthesis, providing powerful tools for the creation of enantiopure silicon-based building blocks and pharmaceuticals.