Dual activation of unsaturated amides with Schwartz's reagent. A diastereoselective access to cyclopentanols and N,O-dimethylcyclopentylhydroxylamines.

The diastereoselective access to cyclopentanols and N,O -dimethylcyclopentylhydroxylamines from 4-pentenoic acid-derived Weinreb amides is described. Based on the concomitant generation of both the nucleophilic and the electrophilic poles by hydrozirconation of the amide and the C=C double bond, the cyclisation may be tuned towards cyclopentanols or N,O -dimethylcyclopentylhydroxylamines depending on the ring-closure promotor. An extension to cis 3-substituted N,O -dimethylcyclohexylhydroxylamines is also presented.