The first example of asymmetric induction in an anionic amino-Cope rearrangement

Article abstract of DOI:10.1016/S0040-4039(98)00487-0

The anionic amino-Cope rearrangement of suitably functionalized acyclic 3-amino-1,5-diene substrates has been achieved and we report the first example of an asymmetric anionic amino-Cope rearrangement to yield an enantiomerically enriched product (75% e.e.). The absolute stereochemistry of the products has been verified and transition state models are proposed to rationalize the stereochemical outcome.