294176-79-7Relevant articles and documents
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 (2007/10/03)
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.
Syntheses of optically active trifluoronorcoronamic acids.
Katagiri,Irie,Uneyama
, p. 2423 - 2425 (2007/10/03)
Syntheses of optically active trifluoronorcoronamic acid 6 and its diastereomer 9 are described. Highly stereospecific and diastereoselective S(N)2 cyclization of gamma-cyanohydrins 3a and 3b gave cyclopropyl nitriles 4a and 4b. Hydrolysis of the cyano gr