Novel Synthesis of 1-substituted meso-3,4-dihydroxypyrrolidines with a RuCl3-catalyzed Key Reaction

Abstract

meso-1-Substituted-3,4-dihydroxypyrrolidines were synthesized in three steps from (Z)-but-2-ene-1,4-diol involving RuCl3-catalyzed cis-dihydroxylation of (Z)-but-2-ene-1,4-diyl dimethanesulfonate. In this key step RuCl3-catalysis allowed us to avoid the use of more toxic OsO4. The final cyclization reaction was performed with three different aromatic amines to yield the desired 3,4- dihydroxypyrrolidines.