562817-58-7Relevant 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
Asymmetric synthesis of (+)-L-733, 060 and (+)-CP-99, 994 based on a new chiral 3-piperidinol synthon.
Huang, Pei-Qiang,Liu, Liang-Xian,Wei, Bang-Guo,Ruan, Yuan-Ping
, p. 1927 - 1929 (2007/10/03)
[reaction: see text] Selective and potent neurokinin substance P receptor antagonists (+)-L-733, 060 (1) and (+)-CP-99, 994 (2) have been synthesized starting from a new (3S)-piperidinol synthon derived from l-glutamic acid. The methods featured a C-2 reg
