Tert-Butyl (1S)-1-(3,5-difluorobenzyl)-2-oxobut-3-enylcarbamate → Tert-Butyl (1S)-1-(3,5-difluorobenzyl)-2-hydroxybut-3-enylcarbamate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([F:22])[CH:21]=1)[CH2:5][C@H:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:7](=[O:10])[CH:8]=[CH2:9].[BH4-].[Na+].[Cl-].[Ce+3].[Cl-].[Cl-]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([F:22])[CH:21]=1)[CH2:5][C@H:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:17])[CH3:15])[CH:7]([OH:10])[CH:8]=[CH2:9]Participants
4
Procedure
Ketone (2) was reduced with sodium borohydride/cerium chloride (Luche conditions) in methanol at 0° C. to provide the allylic alcohol 3 as a mixture of alcohol epimers (white solid).