Asymmetric .ALPHA.-substituted phenethylamines. V. Synthesis of chiral 1-alkyl-2-phenylethylamines via Grignard reaction of 4-phenyl-1,3-oxazolidines.

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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.

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