Lee JH, Gupta S, Jeong W, Rhee YH, * Park J. * Pohang University of Science and Technology, Republic of Korea
Characterization and Utility of N-Unsubstituted Imines Synthesized from Alkyl Azides by Ruthenium Catalysis.
Angew. Chem. Int. Ed. 2012;
51: 10851-10855
Key words
allylation - azides - ruthenium
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%.
