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

Abstract

(2 R,3 R)-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.