Asymmetric synthesis by using the chirality of l-ephedrine. II. Synthesis of (R)-.ALPHA.-phenylethylamine.

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The chiral hydrazone (II), obtained by the condensation of N-aminoephedrine with benzaldehyde, was reacted with Grignard reagent to give the chiral hydrazine (IVa) in almost 100% diastereomeric excess. On the other hand, the chiral hydrazone (III) was reduced by lithium aluminium hydride to give the chiral hydrazine (IV). Hydrogenolysis of the chiral hydrazine (IVa) gave (R)-α-phenylethylamine (Va) with more than 97% optical purity, and l-ephedrine used as a chiral auxiliary reagent was recovered.

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