Catalytic asymmetric synthesis of allylic aryl ethers.
[reaction: see text] The reaction of trichloroacetimidate derivatives of (Z)-2-alken-1-ols with phenol nucleophiles in the presence of the palladium(II) catalyst [COP-OAc]2 provides 3-aryloxy-1-alkenes in high yields and high enantiomeric purity (typically 63-90% yield and 90-97% ee). The reaction is exemplified by 20 examples. The method employs 1 mol % of the commercially available catalysts (S)- or (R)-[COPOAc]2, produces the branched isomer with unprecedented regioselectivity, and is compatible with the presence of base-labile functionality in either reactant.
Kirsch
Stefan F
SF
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Overman
Larry E
LE
White
Nicole S
NS