Skip to main content
. 2004 Mar 30;101(15):5461–5466. doi: 10.1073/pnas.0307443101

Table 1. Allylic alkylation of 1,3-diphenylprop-2-enyl acetate (2) with dimethyl malonate and p5 or p(5-co-8) as ligand.

No. Ligand Pd,* mol% Temp., °C Time, hr Yield, % ee, %
1 (+)-p5 25 40 1 91§ 6.4
2 (+)-p5 10 25 3 85§ 4.7
3 (+)-p5 5 25 6 87§ 6.4
4 (+)-p5 2 25 150 20 5.8
5 (+)-p(5-co-8) 10 25 4.5 83§ 38
6 (+)-p(5-co-8) 25 25 1 84§ 44
7 (+)-p(5-co-8) 25 0 16 99 60
8 (+)-p(5-co-8) 25 -10 64 72 55

Reaction was in CH2Cl2,[Pd]/[repeating units] = 1:1.2.

*

Based on substrate 2.

Yields of isolated product.

Determined by 1H-NMR in the presence of 20 mol % of the chiral shift reagent [Eu(hfc)3], hfc = 3-(heptafluoropropylhydroxymethylene)-d-camphorate. All products were (R)-configured (determined by comparison with ref. 28).

§

Quantitative conversion according to TLC.