5173-74-0Relevant articles and documents
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Brown,H.C.,Negishi,E.
, p. 1224 - 1226 (1969)
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Electroorganic Chemistry. 140. Electroreductively Intra- and Intermolecular Couplings of Ketones with Nitriles
Shono, Tatsuya,Kise, Naoki,Fujimoto, Taku,Tominaga, Naoto,Morita, Hiroshi
, p. 7175 - 7187 (2007/10/02)
Electroreduction of γ- and δ-cyano ketones in i-PrOH with Sn cathode gave α-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products.Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of γ- and δ-cyano ketones in one of the key steps.Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product.The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.
Lanthanides in Organic Synthesis. 3. A General Procedure for Five- and Six-Membered Ring Annulation
Molander, Gary A.,Etter, Jeffrey B.
, p. 1778 - 1786 (2007/10/02)
An improved method for cyclization of 2-(ω-iodoalkyl)cycloalkanones utilizing samarium diiodide (SmI2) has been developed.Both five- and six-membered rings can be constructed in excellent yields for the first time by such a process.The reaction takes place under very mild conditions, allowing toleration of a number of functional groups under the reaction conditions.Stereochemical aspects of the reaction heve been delineated.The reaction has been found to be highly stereoselective when cyclization takes place onto cyclopentanone substrates and when 2-substituted-2-(ω-haloalkyl)cycloalkanone precursors are utilized.