Lautens Mark, Paquin Jean-François
Davenport Chemical Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5H 3H6.
Org Lett. 2003 Sep 18;5(19):3391-4. doi: 10.1021/ol0350238.
[reaction: see text] The 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-Bu(3)PH]BF(4) (2.5-5 mol %), HCO(2)H/Et(3)N (1:2) (3 equiv), CH(3)CN (0.05M), 40 degrees 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 alpha-methyl-beta,gamma-unsaturated aldehyde.
