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Asymmetric Synthesis of Dipropionate Derivatives through Catalytic Hydrogenation of Enantioenriched E-Ketene Heterodimers.

ABSTRACT: A highly diastereoselective approach to dipropionate derivatives through Pd/C-catalyzed hydrogenation of enantioenriched E-ketene heterodimers is described. Catalytic hydrogenation of the E-isomer of ketene heterodimer ?-lactones (12 examples) provides access to syn,anti-?-lactones (dipropionate derivatives) bearing up to three stereogenic centers (dr up to 49:1), and with excellent transfer of chirality (ee up to >99%).

SUBMITTER: Chen S

PROVIDER: S-EPMC5035679 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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Asymmetric Synthesis of Dipropionate Derivatives through Catalytic Hydrogenation of Enantioenriched E-Ketene Heterodimers.

Chen Shi S Mondal Mukulesh M Ibrahim Ahmad A AA Wheeler Kraig A KA Kerrigan Nessan J NJ

Synthesis 20160412 16

A highly diastereoselective approach to dipropionate derivatives through Pd/C-catalyzed hydrogenation of enantioenriched E-ketene heterodimers is described. Catalytic hydrogenation of the E-isomer of ketene heterodimer β-lactones (12 examples) provides access to syn,anti-β-lactones (dipropionate derivatives) bearing up to three stereogenic centers (dr up to 49:1), and with excellent transfer of chirality (ee up to >99%). ...[more]

PMID: 27681860

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