First enantioselective non-biological synthesis of asymmetrised tris(hydroxymethyl)methane (THYM*) and bis(hydroxymethyl)acetaldehyde (BHYMA*)

An asymmetric synthesis of a chiral non-racemic (O-benzyl, O′-silyl) derivative of the latent C3v-symmetric tris(hydroxymethyl)methane (THYM*) and of the bis(hydroxymethyl)acetaldehyde (BHYMA*) in 6 steps, 38% overall yield and 7 steps, 36% overall yield, respectively, is described starting from the commercially available 4-nitrobenzoate derivative of 17. The method involves the Sharpless asymmetric epoxidation and a regioselective copper-mediated oxirane ring opening, as key steps.