Abstract
High stereoselectivity of the Mannich reaction of N,N-phthaloylamino acids as chiral auxiliaries is achieved by choice of the aniline part of the Schiff base 1. Treatment of ortho-substituted N-arylimines of type 1 and N,N-phthaloyl-tert-leucine chloride (2) with a silylketene acetal provides the corresponding Mannich adducts 3 with diastereomer ratios in excess of 99:1.
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