Diastereoselective aldolization of alpha-aminonitriles. Diastereoselective synthesis of beta-amino alcohols and beta,gamma-diamino alcohols.
Aldolization performed by addition of lithiated N-benzyl-N-tert-butylaminoacetonitrile to aldehydes provides diastereomerically pure anti-beta-hydroxy-alpha-aminonitriles. They are transformed into syn,anti-protected beta,gamma-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.
Leclerc
Eric
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Laboratoire de chimie des organoéléments, UMR 7611, Université Pierre et Marie Curie 4, place Jussieu, tr. 44-45 2(ème) ét., 75252 Paris Cedex 05, France.
Vrancken
Emmanuel
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Mangeney
Pierre
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