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Divergent reaction pathways of homologous and isosteric propargyl amides in sequential Ru/Pd-catalyzed annulations for the synthesis of heterocycles.
J Org Chem
April 2013
Department of Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one-pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.
View Article and Find Full Text PDFHighly enantioselective addition of phenylacetylene to aldehydes catalyzed by a camphorsulfonamide ligand.
Org Lett
April 2004
Department of Biochemistry and Molecular Biology, School of Life Science, Lanzhou University, Lanzhou 730000, China.
The asymmetric addition of phenylacetylene to aldehydes was carried out by using a camphorsulfonamide titanium complex as a catalyst. The reactions proceeded under mild conditions and gave the products with good yields and high ees. This system is very useful for the synthesis of chiral propargylic alcohol.
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