Tetrahedron: Asymmetry

Stereoselective route to 15 N-labeled-β-deuterated amino acids: synthesis of (2S, 3R)-[3-2 H, 15 N]-phenylalanine

DW Barnett, MJ Panigot, RW Curley

Index: Barnett, Derek W.; Panigot, Michael J.; Curley Jr., Robert W. Tetrahedron Asymmetry, 2002 , vol. 13, # 17 p. 1893 - 1900

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Citation Number: 10

Abstract

(2S, 3R)-[3-2H, 15N]-Phenylalanine hydrochloride was synthesized utilizing 15N-labeled 8- phenylmenthylhippurate as a chiral glycine equivalent. The key step in the synthesis was the alkylation of the glycine template with (S)-(+)-benzyl-α-d-mesylate. The doubly labeled alkylation product was obtained in 89% yield with 92% de at the α-carbon and 74% de at the β-carbon. The nature of the electrophile employed in the alkylation step significantly ...