137487-58-2Relevant academic research and scientific papers
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
Sutowardoyo,Sinou
, p. 437 - 444 (2007/12/18)
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.
