An unusual kinetic approach to the Pictet–Spengler reaction was investigated, in which l- or d-tryptophan methyl ester reacted with aldehydes of 1,2-O-cyclohexylidene-3-allyloxy-α-d-xylofuranose, yielding exclusively the cis or trans diastereomer of tetrahydro-β-carboline glycoside, respectively, with complete stereocontrol.
Keywords
Pictet–Spengler reaction - stereoselectivity - diastereoselectivity - stereocontrol - glycosides - imines - π-stacking interactions