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

Autor:	Lei Jin, Shuai Zhao, Xin Chen
Jazyk:	angličtina
Rok vydání:	2018
Předmět:	unnatural phenylalanine derivatives phase transfer catalysts asymmetric α-alkylation glycine Schiff base Organic chemistry QD241-441
Zdroj:	Molecules, Vol 23, Iss 6, p 1421 (2018)
Druh dokumentu:	article
ISSN:	1420-3049 23061421
DOI:	10.3390/molecules23061421
Popis:	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.
Databáze:	Directory of Open Access Journals
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