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The sodium salt of (R)-1-[(S)-(diphenylphosphino)ferrocenyl]ethyl mercaptan 1 reacted with racemic epoxide 2 to furnish the P,S,O system 3 as a separable mixture of diastereoisomers. The absolute configuration of (R, S, S)-(S)-4a and that of the palladium π-allyl complex 6a were established by crystal structure determinations.
An enantiomerically enriched cyclopalladated 8-ethylquinoline derivative reacted with dimethyl acetylenedicarboxylate to yield a [2.3.3] cyclazine with virtually the same enantiomeric enrichment. This study provides evidence for a concerted alkyne insertion in the Pd-C bond.
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