(2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)prop-2-enyl diazoacetate → benzyl 4-[(1S,5R,6R)-2-oxo-3-oxabicyclo[3.1.0]hex-6-yl]phenylcarbamate

Participants

Reaction Steps

A solution of (2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)prop-2-enyl diazoacetate (0.7 g, 2.0 mmol) in dichloromethane (20 mL) was added dropwise over 18 h to a refluxing solution of bis-(N-t-butylsalicylaldiminato)copper(II) (0.041 g, 0.01 mmol) in 80 mL of toluene. After the addition was complete, the reaction mixture was heated for another 2 h at reflux and stirred at room temperature for 36 hours. Then the reaction mixture was cooled, filtered and concentrated. The crude oil was purified by silica gel column chromatography (gradient 0-1.5% MeOH-DCM) to provide the title compound and its enantiomer as a racemic mixture.

Provenance & Evidence