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Molecules 2018, 23(6), 1421; https://doi.org/10.3390/molecules23061421

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

School of Pharmaceutical & Life Sciences, Changzhou University, Changzhou 213164, Jiangsu, China
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Academic Editor: Raquel P. Herrera
Received: 24 April 2018 / Revised: 20 May 2018 / Accepted: 24 May 2018 / Published: 12 June 2018
(This article belongs to the Collection Recent Advances in Organocatalysis)
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Abstract

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. View Full-Text
Keywords: unnatural phenylalanine derivatives; phase transfer catalysts; asymmetric α-alkylation; glycine Schiff base unnatural phenylalanine derivatives; phase transfer catalysts; asymmetric α-alkylation; glycine Schiff base
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Jin, L.; Zhao, S.; Chen, X. Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts. Molecules 2018, 23, 1421.

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