Tributyltin Cyanide, a Novel Reagent for the Stereoselective Preparation of 3-Amino-2-hydroxy Acids via Cyanohydrin Intermediates

All articles of this category Reaction of tributyltin cyanide with optically active 2- N -benzyloxyearbonylamino aldehydes 1 gives the corresponding O -tributylstannyl cyanohydrins 2 and 3 stereoselectively. Compounds 2 and 3 are transformed in situ into the methyl 3- N -benzoyloxycarbonyl-amino-2-hydroxy esters 4 and 5 , respectively, via the imidate hydrochloride intermediates. Saponification of 4 and 5 provide 3-amino-2-hydroxy acids 6 and 7 , respectively, key intermediates in the preparation of Bestatin, Amastatin, and analogues.