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

作者：Chen Shi; Mondal Mukulesh; Ibrahim Ahmad A; Wheeler Kraig A; Kerrigan Nessan J^*

来源：Synthesis (Germany), 2016, 48(16): 2619-2626.

DOI：10.1055/s-0035-1561958

• asymmetric synthesis
• ketene heterodimer
• diastereoselectivity
• -lactone
• catalytic hydrogenation

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%).

• 出版日期2016-8