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. Author manuscript; available in PMC: 2012 Dec 30.
Published in final edited form as: Tetrahedron. 2011 Dec 30;67(52):10234–10248. doi: 10.1016/j.tet.2011.10.031

Table 1.

Solvent and ligand effects on enantioselective decarboxylative allylation.a

graphic file with name nihms-332928-f0005.jpg
entry ligand solvent yieldb(%) eec(%)
1 L1 THFe 94 84
2 L1 1,4-dioxane 86 84
3 L1 2-methyl THFe 75 85
4 L1 TBMEe 88 85
5 L1 Et2O 93 86
6 L1 PhH 84 86
7 L1 PhCH3 91 88
8d L2 PhCH3 57 90
9 L3 PhCH3 77 72
a

Conditions: β-ketoester 6a (1.0 equiv), Pd2(pmdba)3 (2.5 mol %), ligand (6.25 mol %) in solvent (0.1 M) at 30 °C; pmdba = 4,4’-methoxydibenzylideneacetone.

b

Isolated yield.

c

Determined by chiral HPLC.

d

Increased catalyst loadings were required to achieve full conversion: Pd2(pmdba)3 (5 mol %), L2 (12.5 mol %).

e

THF = tetrahydrofuran, TBME = tert-butyl methyl ether, 2-methyl THF = 2-methyl tetrahydrofuran.