Heck–Matsuda Reaction for Allylic Nitro Compounds: A Short Asymmetric Synthesis of an FTY720 Derivative

Abstract

AbstractThe 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 Pd2dba3. 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.