Table 2.

Pd-Catalyzed Allylic Alkylation Reaction – Desymmetrization of 1 with 6^a

entry	ligand	yield (%)b	% eec
1	L5a	93	86.2 (−)
2	L5ad	27	92.6 (−)
3	L6e	63	89.5 (+)
4	L7	conv <5%	ndg
5	L8	92	85.5 (+)
6	L9	85	83.0 (+)
7	L10f	76	99.7 (+)
8	L11	conv 0%	ndg
9	L12	conv <5%	ndg
10	L13	conv <5%	ndg
11	L14f	83	99.4 (+)

^aReactions were run with 100 mg (0.31 mmol) of 1, [Pd(allyl)Cl]₂ (2 mol %), a ligand (8 mol %), 6 (1.2 equiv), LDA (1.2 equiv) in THF at − 60 °C for 15 h unless otherwised noted.

^bIsolated yield.

^cEstimated based on the enantiopurity of 9 determined by chiral HPLC analysis using a Daicel Chiralpak AD-RH column.

^dReaction was run with 2.6 equiv of 6 and LDA, which completed in 20 min.

^eReaction run with 2.0 equiv of 6 and LDA.

^fReaction time was 8 h.

^gnd = not determined.