129076-05-7Relevant academic research and scientific papers
Asymmetric allylic amination catalyzed by chiral ferrocenylphosphine-palladium complexes
Hayashi, Tamio,Kishi, Kohei,Yamamoto, Akihiro,Ito, Yoshihiko
, p. 1743 - 1746 (1990)
A palladium complex bearing chiral (hydroxyalkyl)ferrocenylphosphine ligand was found to be a highly regio-and stereoselective catalyst for the asymmetric allylic animation of 2-butenyl acetates with benzylamine, the nucleophilic attack of the amine takin
Enantio- and diastereoselective syntheses of 3-hydroxypiperidines through iridium-catalyzed allylic substitution
Hoecker, Johannes,Rudolf, Georg C.,Baechle, Florian,Fleischer, Steffen,Lindner, Benjamin D.,Helmchen, Guenter
supporting information, p. 5149 - 5159 (2013/11/06)
Stereoselective syntheses of 3-hydroxypiperidines have been developed. Key intermediates are N-protected allylamines that are prepared by an enantioselective iridium-catalyzed allylic amination. A subsequent catch and release procedure that involves an epoxidation and base-mediated elimination yields δ-lactams that are suitably functionalized to prepare biologically active 3-hydroxypiperidines. In addition, applications of this method to the total syntheses of deoxymannojirimycin, D-erythro-sphingosine, and chiral building blocks of interest for medicinal chemistry are described. Stereoselective syntheses of 3-hydroxypiperidines are reported. The key reactions are an iridium-catalyzed allylic amination and a catch and release procedure that consists of a highly diastereoselective epoxidation and a base-mediated ring opening of the epoxide. This method was applied to the total syntheses of sphingosine, deoxymannojirimycin, and pharmaceutically relevant small molecules. Copyright
A highly enantioselective allylic amination reaction using a commercially available chiral rhodium catalyst: Resolution of racemic allylic carbonates
Vrieze, Derek C.,Hoge, Garrett S.,Hoerter, Perrine Z.,Van Haitsma, Jared T.,Samas, Brian M.
supporting information; experimental part, p. 3140 - 3142 (2009/12/06)
A novel method for the kinetic resolution of unsymmetrical acyclic allylic carbonates and the concurrent synthesis of enantioenriched secondary amines using a commercially available chiral catalyst is disclosed.
