Heck-Matsuda reaction for allylic nitro compounds: A short asymmetric synthesis of an FTY720 derivative

Abstract

The Heck-Matsuda reaction for allylic nitro compounds effectively afforded cinnamyl nitro compounds in good yields. Aryldiazonium salts that have an electron-donating substituent underwent a smooth reaction in the presence of Pd 2dba 3. A palladium complex that coordinated with an electron-rich ligand was necessary for the reaction to progress with electron-deficient aryldiazonium salts. An optically active allylic nitro compound underwent reaction without the loss of optical purity at the stereogenic center. A short synthesis of an optically active FTY720 derivative was achieved by this method. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.