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

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 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. Aryl units were introduced to allylic nitro compounds by using the Heck–Matsuda reaction with aryldiazonium salts. The reaction progressed smoothly in the presence of Pd2dba3 with CH3CN as the solvent. The stereochemistry of the stereogenic center at the allylic position was retained throughout the reaction, and a short synthesis of a chiral FTY720 derivative was achieved.