Intermolecular Chirality Transfer from Silicon to Carbon

Significance

This report allows mechanistic insight into the chirality transfer from silicon to carbon under palladium catalysis. Isotope labeling and crossover experiments led to the discovery that the catalytic cycle involves two silicon atoms, one for addition to the substrate and a second to turn over the catalyst and continue the cycle. One of the important factors is the reversibility of the first steps where K ₂ favors the π-bound palladium and K ₃ involves a match(m)-mismatch(mm) situation where k ^m/k ^mm = 3, which explains the high chirality transfer.