Addition of silanethiols to aldehydes and ketones: a simple route to homochiral α-siloxyalkanethiols

In the presence of imidazole as a catalyst, silanethiols R3SiSH react by addition with aldehydes and with ketones that carry electron-withdrawing substituents to give α-siloxyalkanethiols R1R2C(SH)OSiR3. Diastereoselective addition of a silanethiol to an enantiopure aldehyde or ketone provides a convenient route to a homochiral α-siloxyalkanethiol R1R2C*(SH)OSiR3.