170. Asymmetric Palladium-Assisted Alkylation of Alkenes

Article abstract of DOI:10.1002/hlca.19830660615

Palladium-promoted alkylation of alkenes using chiral sulfoxide-containing carbanions and chiral lithiated oxazolines results in asymmetric induction (AI) ranging from 3-5 percent (1,5 induction), 20-40 percent (1,3 induction) to 44-52 percent (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 percent).