Efficient synthesis of (2R,3R)- and (2S,3S)-2,3-diaminobutane-1,4-diol and their dibenzyl ethers

Article abstract of DOI:10.1016/S0957-4166(97)00086-4

(2R,3R)-2,3-Diaminobutane-1,4-diol 6 and its dibenzyl ether 7 were efficiently synthesized starting from L-tartaric acid 1a. The crucial step, debenzylation of intermediate dibenzyloxydiazide 4, was accomplished in good yield by boron trichloride-dimethyl sulfide complex. The enantiomeric series was similarly obtained starting from D-tartaric acid.