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Heck–Matsuda Reaction for Allylic Nitro Compounds: A Short Asymmetric Synthesis of an FTY720 Derivative
Author(s) -
Nakano Toshiki,
Miyahara Mizuki,
Itoh Toshiyuki,
Kamimura Akio
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101703
Subject(s) - chemistry , allylic rearrangement , nitro , stereocenter , heck reaction , substituent , derivative (finance) , ligand (biochemistry) , medicinal chemistry , palladium , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , alkyl , biochemistry , receptor , financial economics , economics
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 2 dba 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.