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Communication | Special issue | Vol 30, No. 1, 1990, pp.287-290
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S35
■ Asymmetirc Induction by Chiral Heterocyclic Compounds: Highly Diastereoselective Reaction of 5-Oxa-7,8a-diazaperhydroazulen-8-ones with Organometallic Reagents

Hiroshi Takahashi,* Ichiro Morimoto, and Kimio Higashiyama

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

1) New chiral heterocyclic compounds, 5-oxa-7,8a-diazaperhydroazulen-8-ones (3a-c), were synthesized from (S)-prolinol (1) and potassium cyanate, followed by the condensation with aldehydes. 2) Extremely high diastereoselective reaction of the 3a-c with diethylzinc proceeded with a facil procedure to give (2S, 1’S)-N-1’-arylpropyl-2-hydroxymethyl-1-pyrrolidinecarboxamide (4a-c). 3) The reduction of 4a-c with Red-Al gave (S)-1-aryl-N-methylpropylamines (5a-c) and (S)-prolinol (1) in good yields.