Asymmetric Synthesis of Dipropionate Derivatives through Catalytic Hydrogenation of EnantioenrichedE-Ketene Heterodimers.
A highly diastereoselective approach to dipropionate derivatives through Pd/C-catalyzed hydrogenation of enantioenrichedE-ketene heterodimers is described. Catalytic hydrogenation of theE-isomer of ketene heterodimer β-lactones (12 examples) provides access tosyn,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%).
Department of Chemistry, Oakland University, 2200 N. Squirrel Road, Rochester, MI 48309-4477, USA.
Shi
S
Chen
Department of Chemistry, Oakland University, 2200 N. Squirrel Road, Rochester, MI 48309-4477, USA.
Mukulesh
M
Mondal
Department of Chemistry, Oakland University, 2200 N. Squirrel Road, Rochester, MI 48309-4477, USA.
Ahmad A
AA
Ibrahim
Department of Chemistry, Eastern Illinois University, 600 Lincoln Avenue, Charleston, IL 61920-3099, USA.
Kraig A
KA
Wheeler
Department of Chemistry, Oakland University, 2200 N. Squirrel Road, Rochester, MI 48309-4477, USA.
Nessan J
NJ
Kerrigan
asymmetric synthesis; catalytic hydrogenation; diastereoselectivity; ketene heterodimer; β-lactone
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