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Formation of a Quaternary Carbon Center through the Pd(0)/PhCOOH-Catalyzed Allylation of Cyclic β-Keto Esters and 1,3-Diketones with Alkynes
journal contribution
posted on 2004-09-17, 00:00 authored by Nitin T. Patil, Yoshinori YamamotoFormation of a quaternary carbon center through
the allylation of β-keto esters and 1,3-diketones with alkynes
is accomplished by the use of Pd(0)/benzoic acid catalyst.
Reactions of various cyclic β-keto esters and 1,3-diketones
with alkynes in the presence of Pd2dba3·CHCl3 (5 mol %),
PPh3 (40 mol %), and PhCOOH (10 mol %) proceeded at
100 °C in toluene (5 M) to give the corresponding allylation
products in high yields in a regio- and stereoselective
manner. The possibility of asymmetric allylation is also
discussed.