Thermal rearrangement of enantioenriched α-hydroxy imines -I. Enantiocontrolled synthesis of α-substituted α-amino ketones

Article abstract of DOI:10.1016/0040-4039(95)00680-B

Enantioenriched 2-allyl- and 2-(3-trimethylsilylpropargyl)-2-hydroxycyclohexanone were respectively obtained by resolution from the corresponding diastereomeric acetal derived from C₂-symmetrical diol or from the camphanate ester. Study of the rearrangement of their corresponding imine derivatives has shown that it occurred with complete retention of the stereogenicity.