Ring-opening of glycidyl derivatives by silanes mediated by Ti(O-i-Pr)4 or Al(O-i-Pr)3: Access to versatile C3 building blocks

Article abstract of DOI:10.1016/S0957-4166(00)82168-0

Ring-opening of chiral glycidol or glycidyl tosylate by Me₃SiN₃ or Me₃SiCN catalyzed by Ti(O-i-Pr)₄ or Al(O-i-Pr)₃ occurred in a regiospecific manner and with very high stereoselectivity, leading to new trifunctionalized chiral building blocks. The enantiomeric excess of the ring-opened products was 90-95%, as determined by ¹H NMR of the Mosher ester derivatives, indicating that there was no significant loss of optical purity during the ring-opening. This methodology was applied for the one-pot synthesis of (R)-1-azido-3-naphthyloxy-2-hydroxypropane in 94% ee, a precursor of analogs of propranolol.