Asymmetric Palladium-Assisted Alkylation of Alkenes

Palladium-promoted alkylation of alkenes using chiral sulfoxide-containing carbanions and chiral lithiated oxazolines results in asymmetric induction (AI) ranging from 3–5% (1,5 induction), 20–40% (1,3 induction) to 44–52% (1,4 induction). No general trend allowing predictions of results was found. With 1-hexene, attack at C(1) is almost exclusive but propene gives a mixture of attack at C(1) and C(2). The use of a chiral ligand together with malonate anion also leads to some asymmetric induction (ca. 20%).