Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 3, Pages 502-503Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja067780h
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A two-silicon cycle for the highly efficient intermolecular chirality transfer from silicon to carbon (98-99% ct) in the palladium-catalyzed hydrosilylation of norbornenes emerges from an investigation involving catalytic crossover experiments with isotopically labeled silicon-stereogenic silanes. A key outcome of these experiments, which are supported by product-distribution modeling, is the conclusion that the chirality transfer arises from thermodynamically controlled reversible silapalladation of the alkene rather than from kinetic control during irreversible -bond metathesis of the resulting -silyl -alkyl palladium complex with chiral silane.
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