Chen, S;Mondal, M;Ibrahim, AA;Wheeler, KA;Kerrigan, NJ

2016

August

Synthesis (Germany)

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

Published

0 ()

DIASTEREOSELECTIVE ALDOL REACTIONS METHYL CHIRAL ALDEHYDES NATURAL-PRODUCTS ENANTIOSELECTIVE ADDITION POLYPROPIONATE SYSTEMS BETA-LACTONES (-)-PIRONETIN DIMERIZATION POLYKETIDES KETOKETENES

48

2619

2626

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%).

STUTTGART

0039-7881

10.1055/s-0035-1561958