160924-04-9Relevant articles and documents
Addition of dilithiated methyl-3-aminobutanoate to aldehydes proceeds with ul-1,2-induction
Ettmayer, Peter,Huebner, Michael,Gstach, Hubert
, p. 3901 - 3904 (2007/10/02)
Syntheses of 2-substituted 1-hydroxyethylene building blocks, useful as the central moiety of HIV-1 protease inhibitors, is described. Dilithiated N-protected-3-amino-4-phenylbutanoic methyl esters are reacted with aldehydes to give predominantly aldol products with l,u configuration. The diastereomeric ratio depends on the N-protecting group and on the experimental conditions. The configurations are assigned by 1H-NMR of cyclic derivatives and are supported by X-ray structure.