Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(0) catalyst. The reaction proceeded predominantly with 1,3 transposition and with inversion of configuration due probably to a prior isomerization from anti to syn-π-allylpalladium intermediate (14→15). The stereochemistry observed in the reaction with phenylzinc chloride was opposite to that with the soft nucleophile.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry