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Synfacts 2013; 9(1): 0079
DOI: 10.1055/s-0032-1317740
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Ruthenium-Catalyzed Generation of N-Unsubstituted Imines

Contributor(s):
Paul Knochel
,
Andreas K. Steib
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
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Publication History

Publication Date:
17 December 2012 (online)

 
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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.


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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%.


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