54723-26-1Relevant academic research and scientific papers
Enantioselective synthesis of Indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2 + 2 + 2] cycloaddition of alkenyl Isocyanates and terminal alkynes
Lee, Ernest E.,Rovis, Tomislav
supporting information; body text, p. 1231 - 1234 (2009/04/07)
An enantioselective synthesis of Indolizidines bearing quaternary substituted stereocenters by way of a rhodium-catalyzed [2 + 2 + 2] cycloaddition of substituted alkenyl Isocyanates and terminal alkynes Is described. The reaction provides lactam products using aliphatic alkynes, whereas aryl alkynes give rise to vlnylogous amide products. Through modification of the phosphoramldlte llgand, high levels of enantloselectlvlty, regloselectlvlty, and product selectivity are obtained for both products.
Metallic Nickel-Mediated Synthesis of Ketones by the Reaction of Benzylic, Allylic, Vinylic, and Pentafluorophenyl Halides with Acid Halides
Inaba, Shin-ichi,Rieke, Reuben D.
, p. 1373 - 1381 (2007/10/02)
Metallic nickel was investigated as a convenient coupling reagent for the synthesis of ketones by the reaction of benzylic, allylic, vinylic, and pentafluorophenyl halides with acid halides at 85 deg C in glyme.A variety of benzylic ketones with functional groups including halogen, cyano, methoxycarbonyl, and hydroxycarbonyl groups were prepared in good yields by this method.The reaction was demonstrated to proceed via organonickel halide intermediates formed by the smooth oxidative addition of benzylic and acyl halides to metallic nickel, which were trapped with electron-deficient olefins. (?-Allyl)nickel halides, prepared in situ at 85 deg C from allylic halides and the nickel, also worked for the preparation of ketones.Vinylic and pentafluorophenyl halides but not alkyl halides reacted with acid halides to give the corresponding ketones in moderate yields.
