Disiloxane → 2-Phenyl-1-propanol

Participants

Reaction Steps

Furthermore, the purificative deprotections of the chiral silylethers (1f and 1m) were examined in the presence of the corresponding enantiomerically pure alcohols using the triphasic system of FIGS. 2 and 3. The deprotection reaction of 1f (1.0 equiv) proceeded in the presence of (R)-(+)-1-(2-naphthyl)ethanol (1.0 equiv), and 1-(2-naphthyl)ethanol was obtained in 83% total yield in a ratio with 41/59 in P-/S-phases (entry 5). The enantiomeric excess (ee) values of 1-(2-naphthyl)ethanol obtained were >97% and 90% in P- and S-phases, respectively. The chiral silyl ether 1m (1.0 equiv) also underwent the purificative deprotection in the presence of (S)-(−)-2-phenylpropanol (1.0 equiv), and 2-phenylpropanol was obtained in 76% total yield in a ratio with 39/61 in P/S-phases. The ee values of 2-phenylpropanol were 89% and 87% in P- and S-phases, respectively.

Provenance & Evidence