Hydroboration of vinylsilanes with BH3 affords two silylethanol regioisomers. Here, we investigated the regioisomeric ratio of hydroboration products from various vinylsilanes, focusing on the characteristic reaction profile. All investigated vinylsilanes afforded both regioisomers, and greater bulkiness increased the proportion of Markovnikov products. The obtained silylethanols were used as hydrophobic building blocks for constructing nuclear progesterone receptor (PR) modulators. Notably, structural conversion from α-isomer (silylethan-1-oxy derivative) to β-isomer (2-silylethoxy derivative) caused complete activity-switching from PR agonist to antagonist. Our results indicate that silylethanols are useful for structural development, and vinylsilanes are a versatile source of hydrophobic building blocks for biofunctional molecules.

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