Benzaldehyde → trans-4-Methoxycarbonyl-5-phenyl-2-oxazoline
Reaction equation
C[CH:2]([N+:7]#[C-:8])[C:3]([O:5][CH3:6])=[O:4].[CH:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH3:6][O:5][C:3]([C@H:2]1[C@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:16][CH:8]=[N:7]1)=[O:4]Participants
3
Procedure
Methyl α-methylisocyano-acetate was reacted with benzaldehyde in the presence of the same catalyst and under the same reaction conditions of those of Example 2. After the solvent was concentrated, the reaction mixture was subjected to silica-gel column chromatography to obtain trans-4-methoxycarbonyl-5- phenyl-2-oxazoline and the corresponding cis-form in a ratio of 87/13). Total yield: 90%. The optical purity of the trans-(4S,5R) form was measured in the same manner as in Example 1, which was 93% ee.
Workup
- concentrationAfter the solvent was concentrated