Resolution of 2-aryloxy-1-propanols via lipase-catalyzed enantioselective acylation in organic media

Resolution of 2-phenoxy-1-propanols through the enantioselective acylation mediated byAchromobactersp. lipase as biocatalyst

“…The reason for choosing vinyl butanoate instead of butanoic anhydride was the ease of comparing the results with those obtained before using Pseudomonas sp. lipase as a biocatalyst (Miyazawa et al 2001a). The results are shown in Table IV.…”

“…b Enantiomeric excess of the remaining alcohol, whose preferred absolute configuration is R . earlier (Miyazawa et al 2000(Miyazawa et al , 2001a, indicate that acyl donors largely affect the lipase's enantioselectivity both sterically and electronically. Next, the enzymatic acylation of 1a was investigated using different acid anhydrides as acyl donors in diisopropyl ether.…”

“…Racemic 2-phenoxy-1-propanols were prepared by the reduction of the corresponding 2-phenoxypropanoic acids using borane Átetrahydrofuran complex (Miyazawa et al 2001a). Authentic samples of the alkanoates of racemic 2-phenoxy-1-propanols were prepared by the acylation of each 2-phenoxy-1-propanol with the corresponding alkanoic acid chloride in the presence of pyridine in dichloromethane.…”

“…We have already reported the resolution of 2-phenoxy-1-propanols through the Pseudomonas sp. lipase-catalyzed enantioselective acylation (Miyazawa et al 2001a). The present paper describes the results of a similar investigation employing the little-known lipase from Achromobacter sp.…”

Enzymatic resolution of tetrahydroisoquinoline derivatives in batch and continuous-flow systems

“…Sakai et al 19 presented a noteworthy 'low-temperature method' for the enzymatic There have also been literature reports of the lipase PS-catalysed O-acylation of primary alcohols with moderate E (< 100). [28][29][30][31][32][33][34][35][36][37][38][39][40][41][42] Another large group of primary alcohols is the family of N-hydroxymethylated β-lactams. The lipase PS-catalysed acylation of the N-hydroxymethylated β-lactams resulted in a relatively large range for E, depending on the type of subtrate.…”