299172-62-6Relevant articles and documents
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
, 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