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Enantioselective alkylation of chiral amide enolates derived from L-prolinol with β-branched chiral iodides afforded good yields of hydroxy amide adducts, which were elaborated in four steps to give C-carboxyalkyl dipeptide inhibitors of stromelysin-1 (MMP-3).
Readily available members of the family of chiral non-racemic aminonaphthols related to the Betti base 1 were tested as complexing agents in the catalytic enantioselective addition of diethylzinc to aryl aldehydes. The use of these bases gave high ee values (up to >99%). The highest ee values were obtained with the tertiary aminonaphthol 2. An important role was played by the solvent. The effect...
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