Chelation control in the ring opening and organometallic addition of α,β-epoxy aldehydes:: a new entry to amino dihydroxyethylene dipeptide isostere subunits

Selective ring opening and subsequent organometallic addition to alpha,beta-epoxy aldehydes is found to afford anti-syn 3-bromo-1,2-diols in high stereo and chemical yield. This sequence is utilized for the enantioselective synthesis of (2S,3R,4R)-2-amino-1-cyclohexyl-6-methylheptane-3,4-diol (an isomer of the Abbott amino diol).