Borane-Catalyzed Chemoselective and Enantioselective Reduction of 2-Vinyl-Substituted Pyridines
Herein, we report that highly chemoselective and enantioselective reduction of 2-vinyl-substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro-bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade process involving 1,4-hydroboration followed by transfer hydrogenation of a dihydropyridine intermediate. The retained double bond in the reduction products permits their conversion to natural products and other useful heterocyclic compounds by simple transformations.
HOMOLYTIC PYRIDYLETHYLATION OF CYCLOHEXANE AND TETRALIN
The homolytic pyridylethylation of cyclohexene and tetraline with 2-vinylpyridine under conditions of peroxide and thermal initiation was investigated.In addition to the main reaction products, i.e., cycloalkylethylpyridines (1 : 1 adducts), compounds indicating rearrangement of the radicals with H migration were also isolated and identified.
Il'yasov, E.A.,Galust'yan, G.G.
p. 326 - 330
(2007/10/02)
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