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Synfacts 2008(1): 0027-0027
DOI: 10.1055/s-2007-991461
DOI: 10.1055/s-2007-991461
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Gold-Catalyzed Three-Component Synthesis of Aminoindolizines
B. Yan, Y. Liu*
Shanghai Institute of Organic Chemistry, P. R. of China
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
18. Dezember 2007 (online)
Significance
Reported is a three-component, Au(III)-catalyzed coupling-heteroannulation reaction of pyridine-2-aldehyde with amines (or amino acids) and alkynes to give aminoindolizines. Optical purity was retained in the products for reactions of chiral amino acids. While secondary amines participate well in this interesting sequence, primary amines fail to give the indolizidine products. Copper catalysis under the same reaction conditions failed. The present method shows ‘green’ advantages since it is a one-step procedure either under solvent-free conditions or in water. The substrate scope was not sufficiently explored.