Asymmetric α-Substituted Phenethylamines. V. Synthesis of Chiral 1-Alkyl-2-phenylethylamines via Grignard Reaction of 4-Phenyl-1, 3-oxazolidines

Abstract

Chiral N-methyl-4-phenyl-1, 3-oxazolidines (2a-e) having a methyl, ethyl, benzyl, isopropyl, and cyclohexyl group at the 2-position of the 1, 3-oxazolidine ring were synthesized. Reactions of 2a-e with Grignard reagents gave (1R, 1'R)- and (1S, 1'R)-1-alkyl-and 1-cycloalkyl-N-2'-hydroxy-1'-phenylethyl-2-phenylethylamines (3a, 3b, 3d, 3e). The absolute configurations of (1R, 1'R)-3a and-3e were determined. (R)-1-Methyl-and (R)-1-cyclohexyl-2-phenylethylamines (4a, 4e) were obtained in high yield by hydrogenolysis of (1R, 1'R)-3a and -3e.