Abstract
AbstractChelated enolates of amino acid derivatives were found to be excellent nucleophiles for stereoselective palladium‐catalyzed allylic alkylations via terminal π‐allyl complexes. Neither the olefin geometry (linear substrates) nor the configuration of secondary allylic substrates has an influence on the newly formed stereogenic centre of the amino acid. This is exclusively controlled by the protecting group on the chiral centre. Therefore, depending on the protecting group used, both diastereomeric amino acids can be obtained in a highly stereoselective fashion (up to 96% ds for 1,5 induction) from one allylic alcohol.
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