Asymmetric α-Substituted Phenethylamines. II. The Enantioselective Synthesis of 1-Aryl-2-phenylethylamines from L- and D-Amino Acids by Means of 1,3-Asymmetric Induction

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概要

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• Optically pure (1S, 1'S)-1-aryl-N-(1'-alkyl-2'-hydroxyethyl)-2-phenylethylamines (13-21) were synthesized from L-alanine, L-leucine, and L-isoleucine via (S)-2-aminoalkanols (1-3) and (E)-(S)-N-(1-alkyl-2-hydroxyethyl) arylmethylideneamines (4-12). On the other hand, the amines with (1R, 1'R) configuration (33-38) were synthesized from D-amino acids, i.e., D-alanine and D-leucine. The absolute configurations of these amines were confirmed by the aromatic quadrant-sector rule. The asymmetric reactions of chiral azomethines (7-12 and 30-32) with benzylmagnesium chloride were found to be extremely highly stereoselective. However, the reactions of the azomethines (4-6 and 27-29) derived from L- and D-alanine with the Grignard reagent afforded poor stereoselectivity.

• 社団法人日本薬学会の論文
• 1983-01-25

著者

• 高橋 浩

  Faculty Of Pharmaceutical Science Hoshi University

• 鈴木 雄二

  Kaken Pharmaceutical Co., Ltd.

• 鈴木 雄二

  Hoshi College Of Pharmacy

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