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Iron-catalyzed asymmetric epoxidation of ?,?-disubstituted enones.

ABSTRACT: The combination of Fe(OTf)(2) and novel phenanthroline ligands enables the catalytic asymmetric epoxidation of acyclic ?,?-disubstituted enones, which have been a heretofore inaccessible substrate class. The reaction provides highly enantioenriched ?,?-epoxyketones (up to 92% ee) that can be further converted to functionalized ?-ketoaldehydes with an all-carbon quaternary center.

SUBMITTER: Nishikawa Y 

PROVIDER: S-EPMC3116448 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Iron-catalyzed asymmetric epoxidation of β,β-disubstituted enones.

Nishikawa Yasuhiro Y   Yamamoto Hisashi H  

Journal of the American Chemical Society 20110516 22

The combination of Fe(OTf)(2) and novel phenanthroline ligands enables the catalytic asymmetric epoxidation of acyclic β,β-disubstituted enones, which have been a heretofore inaccessible substrate class. The reaction provides highly enantioenriched α,β-epoxyketones (up to 92% ee) that can be further converted to functionalized β-ketoaldehydes with an all-carbon quaternary center. ...[more]

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