31053-44-8Relevant academic research and scientific papers
Gold-Catalyzed Hydrohydrazidation of Terminal Alkynes
Zimin, Dmitry P.,Dar'In, Dmitry V.,Rassadin, Valentin A.,Kukushkin, Vadim Yu.
supporting information, p. 4880 - 4884 (2018/08/24)
Facile gold-catalyzed hydrohydrazidation of alkynes with various hydrazides R2CONHNH2 (R = Alk or Ar; including those with an additional nucleophilic moiety) in the presence of Ph3PAuNTf2 (6 mol %) leading to a wide range of substituted keto-N-acylhydrazones (18 examples) in excellent to good yields (99-66%) is reported. This novel metal-catalyzed coupling proceeds under mild conditions (chlorobenzene, 60 °C), exhibits high functional group tolerance, and is insensitive to the electronic and steric effects of the substituents in the reactants.
Enantioselective Allylation of Ketone-Derived Benzoylhydrazones: Practical Synthesis of Tertiary Carbinamines
Berger, Richard,Duff, Keiko,Leighton, James L.
, p. 5686 - 5687 (2007/10/03)
A highly practical method for the enantioselective allylation of ketone-derived benzoylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of benzoylhydrazones to give the hydrazide products with
Stereoselective synthesis of both syn- and anti-N-tert-alkylamines using highly stereospecific crotylation of ketone-derived acylhydrazones with crotyltrichlorosilanes
Ogawa, Chikako,Sugiura, Masaharu,Kobayashi, Shu
, p. 5359 - 5364 (2007/10/03)
Crotyltrichlorosilanes reacted with ketone-derived N-benzoylhydrazones in DMF without any catalyst. This is the first example of highly stereospecific crotylation of ketimine analogues leading to both syn- and anti-N′-tert-alkyl-N-benzoylhydrazines. Different reactivities between (Z)- and (E)-crotylsilanes in terms of yields and selectivities were observed. A kinetic study with both geometrically pure (Z)- and (E)-crotylsilanes was performed. These reactions are most likely to proceed via a cyclic chairlike transition state where the aromatic group of hydrazones takes an axial position. Both diastereomers of allylation products can be converted to the corresponding α,α-disubstituted homoallylic amines without epimerization.
Catalytic asymmetric reductive amination of ketones via highly enantioselective hydrogenation of the C=N double bond
Burk, Mark J.,Martinez, Jose P.,Feaster, John E.,Cosford, Nick
, p. 4399 - 4428 (2007/10/02)
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.
