487065-49-6Relevant academic research and scientific papers
Diastereoselective aldolization of α-aminonitriles. Diastereoselective synthesis of β-amino alcohols and β,γ-diamino alcohols
Leclerc, Eric,Vrancken, Emmanuel,Mangeney, Pierre
, p. 8928 - 8937 (2002)
Aldolization performed by addition of lithiated N-benzyl-N-tert-butylaminoacetonitrile to aldehydes provides diastereomerically pure anti-β-hydroxy-α-aminonitriles. They are transformed into syn,anti-protected β,γ-diamino alcohols by a two-step procedure, involving addition of a Grignard reagent and reduction. The cleavage of the N-tert-butyl group is achieved by a simple acidic treatment. The application of this methodology to chiral, nonracemic aldehydes is studied. Starting from D-isopropylideneglyceraldehyde, an anti, anti, syn, anti-(2R,3S,4S,5R,6R)-diaminotriol is prepared in acceptable yield and with a good level of diastereoselectivity.
