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. [ABSTRACT FROM AUTHOR]