- Asymmetric induction by chiral heterocyclic compounds: highly diastereoselective reaction of 5-oxa-7,8a-diazaperhydroazulen-8-ones with organometallic reagents
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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.
- Takahashi, Hiroshi,Morimoto, Ichiro,Higashiyama, Kimio
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p. 287 - 290
(2007/10/02)
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