- Efficient [(NHC)Au(NTf2)]-catalyzed hydrohydrazidation of terminal and internal alkynes
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The efficient hydrohydrazidation of terminal (6a–r, 18 examples, 0.1–0.2 mol % [(NHC)Au(NTf2)], T = 60 °C) and internal alkynes (7a–j, 10 examples, 0.2–0.5 mol % [(NHC)Au(NTf2)], T = 60–80 °C) utilizing a complex with a sterically demanding bispentiptycenyl-substituted NHC ligand and the benign reaction solvent anisole, is reported.
- Heidrich, Maximillian,Plenio, Herbert
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- Catalytic asymmetric reductive amination of ketones via highly enantioselective hydrogenation of the C=N double bond
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We describe a convenient, chemoselective asymmetric reductive amination procedure for the conversion of ketones to chiral hydrazines and amines. The key step in the three-step process is enantioselective DuPHOS-Rh-catalyzed hydrogenation of the C=N double bond of N-acylhydrazones. Detailed optimization studies revealed the effect of solvent, temperature, and the N- acyl group on the enantioselectivity and catalytic efficiency of the reaction. The reduction products, N-acylhydrazines, were converted to hydrazines or amines through hydrolysis or treatment with samarium(II) iodide, respectively.
- Burk, Mark J.,Martinez, Jose P.,Feaster, John E.,Cosford, Nick
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p. 4399 - 4428
(2007/10/02)
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