Aldehyde and ketone homologations, such as the Tiffeneau–Demjanov–Tchoubar rearrangement with diazo-ACHTUNGTRENNUNGmethane are well studied reactions and lead to various products depending on the nature of substrates and reaction conditions.[1] Employment of trimethylsilyldiazomethane (TMSDM)[2] instead of CH2N2 makes the reactions safer and allows us to capitalize on the rearrangement of the resulting b- ...