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A practical synthesis of both enantiomers of unnatural phenylalanine derivatives by using two pseudoenantiomeric phase transfer catalysts is described. Through asymmetric α-alkylation of glycine Schiff base with substituted benzyl bromides and 1-(bromomethyl)naphthalene under the catalysis of O -allyl- N -(9-anthracenmethyl) cinchoninium bromide ( 1f ) and O -allyl- N -(9-anthracenylmethyl)cinchonidium bromide ( 1i ), respectively, a series of both ( R )- and ( S )-enantiomers of unnatural α-amino acid derivatives were obtained in excellent yields and enantioselectivity. The synthetic method is simple and scalable, and the stereochemistry of the products is fully predictable and controlled: the cinchonine-type phase transfer catalyst 1f resulted in ( R )-α-amino acid derivatives, and the cinchonidine-type phase transfer catalyst 1i afforded ( S )-α-amino acid derivatives.

molecules/molecules online/molecules annual

Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts