Abstract
Regio- and stereoselective α-alkylation of N-terminal amino acid residue of peptides was achieved by Li +-mediated alkylation of aldimines prepared from the peptides and a pyridoxal model compound having a chiral ansa-structure and an ethoxyethoxy group at C-3. The stereochemistry and stereoselectivity of the reaction were found to be influenced predominantly by the chirality of the model compound and Li +, but little by the stereochemistry of the original peptides.
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