ol0350238_si_001.pdf (5.62 MB)
Diastereoselective Palladium-Catalyzed Formate Reduction of Allylic Carbonates as a New Entry into Propionate Units
journal contribution
posted on 2003-08-27, 00:00 authored by Mark Lautens, Jean-François PaquinThe diastereoselective palladium-catalyzed formate reduction of allylic carbonates is described. Reduction of allylic carbonates under mild
conditions (Pd(OAc)2 (2.5−5 mol %), [n-Bu3PH]BF4 (2.5−5 mol %), HCO2H/Et3N (1:2) (3 equiv), CH3CN (0.05M), 40 °C) affords the terminal olefin
as the syn isomer in good yields and modest to excellent diastereoselectivity. These compounds, which are useful building blocks for the
synthesis of polypropionate units, are the synthetic equivalent of the products obtained from an aldol reaction of an α-methyl-β,γ-unsaturated
aldehyde.