4-Nitrobenzoic Acid → ((R)-2-Hydroxy-pent-4-enyl)-carbamic Acid benzyl ester

Participants

Reaction Steps

To a solution of 2-allyl-oxirane (Synthesis 1986, 309; 918 mg, 10.9 mmol) in TBME (12 mL) were added benzyl carbamate (750 mg, 4.96 mmol), 4-nitrobenzoic acid (146 mg, 0.87 mmol) and (1S,2S)-(+)-N—N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 264 mg, 0.44 mmol) at RT, then after 72 h the reaction mixture was partitioned between TBME and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane-EtOAc gradient) produced the title compound (694 mg, 48%). Brown oil, MS: 236.2 (M+H)+.

Provenance & Evidence