Characterization and utility of N-unsubstituted imines synthesized from alkyl azides by ruthenium catalysis.

Significance: The authors report, that N-unsubstituted imines can be efficiently generated from alkyl azides using a ruthenium catalyst and fluorescent light. Furthermore, an allylation reaction in a one-pot fashion was achieved, leading to homoallylic imines. Comment: The mild reaction conditions allow an asymmetric allylation of in situ generated benzaldimine from benzyl azide. Using the chiral allyl bis(isopinocampheyl)borane reagent at –78 °C furnishes the homoallylic amine in 87% yield with an enantiomeric excess of 89%. R1 R2 N3 catalyst A or B (1–2 mol%)