128269-65-8Relevant articles and documents
Asymmetric induction by chiral heterocyclic compounds: highly diastereoselective reaction of 5-oxa-7,8a-diazaperhydroazulen-8-ones with organometallic reagents
Takahashi, Hiroshi,Morimoto, Ichiro,Higashiyama, Kimio
, p. 287 - 290 (2007/10/02)
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.