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Highly Stereoselective Asymmetric Aldol Routes to tert-Butyl-2-(3,5-difluorophenyl)-1-oxiran-2-yl)ethyl)carbamates: Building Blocks for Novel Protease Inhibitors.

ABSTRACT: Enantioselective syntheses of tert-butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate and ((S)-2-(3,5-difluorophenyl)-1-((R)-oxiran-2-yl)ethyl)carbamate are described. We utilized asymmetric syn- and anti-aldol reactions to set both stereogenic centers. We investigated ester-derived Ti-enolate aldol reactions as well as Evans' diastereoselective syn-aldol reaction for these syntheses. We have converted optically active ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate to a potent ?-secretase inhibitor.

SUBMITTER: Ghosh AK 

PROVIDER: S-EPMC5765997 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Highly Stereoselective Asymmetric Aldol Routes to <i>tert</i>-Butyl-2-(3,5-difluorophenyl)-1-oxiran-2-yl)ethyl)carbamates: Building Blocks for Novel Protease Inhibitors.

Ghosh Arun K AK   Cárdenas Emilio L EL   Brindisi Margherita M  

Tetrahedron letters 20170914 43

Enantioselective syntheses of <i>tert</i>-butyl ((<i>S</i>)-2-(3,5-difluorophenyl)-1-((<i>S</i>)-oxiran-2-yl)ethyl)carbamate and ((<i>S</i>)-2-(3,5-difluorophenyl)-1-((<i>R</i>)-oxiran-2-yl)ethyl)carbamate are described. We utilized asymmetric <i>syn</i>- and <i>anti</i>-aldol reactions to set both stereogenic centers. We investigated ester-derived Ti-enolate aldol reactions as well as Evans' diastereoselective <i>syn</i>-aldol reaction for these syntheses. We have converted optically active ((<  ...[more]

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