31053-44-8Relevant articles and documents
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.
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.
