Stereocontrolled synthesis of α,α-disubstituted α-aminoaldehydes and α-aminoacids using a [3,3] allylic trichloracetimidate rearrangement

Article abstract of DOI:10.1016/0040-4039(96)00393-0

Sigmatropic rearrangement of trichloracetimidates derived from syn monoprotected allylic diols 3 resulting from the condensation of vinylalanes or cuprates with α-alkoxyaldehydes afforded diastereomerically pure allylic amines 6. The oxidative cleavage of these amines allowed the access to α,α-disubstituted α-aminoacids in high enantiomeric purity.