kinetic resolution through transesterification using acylase I from Aspergillus sp. and vinyl butyrate;

1: kinetic resolution through transesterification using acylase I from Aspergillus sp. and vinyl butyrate 2: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 90 min, 2.) CH2Cl2, from -70 deg C to RT 3: 76 percent / KMnO4, MgSO4 / acetone / 0.5 h / Ambient temperature View Scheme

oxalyl dichloride; dimethyl sulfoxide; triethylamine in dichloromethane

1: With acylase I from Aspergillus species in toluene T=20°C; 6 h; Enzymatic reaction; 2: With phosphate buffer; acylase I from Aspergillus species in water T=20°C; pH=7.0; 7 h; Enzymatic reaction;

acylase I from Aspergillus species in toluene T=20°C; 6 h; Enzymatic reaction; Title compound not separated from byproducts;

triethylamine in dichloromethane T=0°C;

1: kinetic resolution through transesterification using acylase I from Aspergillus sp. and vinyl butyrate 2: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 90 min, 2.) CH2Cl2, from -70 deg C to RT 3: 1.) BuLi / 1.) hexane, THF, 0 deg C, 30 min, 2.) hexane, THF, from -70 deg C to RT overnight 4: H2 / 10percent Pd/C / methanol / 6 h / 2327.2 Torr View Scheme