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Ruthenium-Catalyzed Cycloisomerization-6-Cyclization: A Novel Route to Pyridines

Barry M. Trost* and Alicia C. Gutierrez

*Department of Chemistry, Stanford University, Stanford, California 94305-5080, Email: bmtroststanford.edu

B. M. Trost, A. C. Gutierrez, Org. Lett., 2007, 9, 1473-1476.

DOI: 10.1021/ol070163t (free Supporting Information)


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Abstract

Conversion of unsaturated ketones and aldehydes derived from the cycloisomerization of primary and secondary propargyl diynols in the presence of [CpRu(CH3CN)3]PF6 to 1-azatrienes and a subsequent electrocyclization-dehydration provides pyridines with excellent regiocontrol.

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Key Words

Cyclopentenes, 2,5-Dihydrofurans, Pyridines


ID: J54-Y2007-1060