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Stereoselective Synthesis of 3‐Alkylideneoxindoles using Tandem Indium‐Mediated Carbometallation and Palladium‐Catalyzed Cross‐Coupling Reactions
Author(s) -
Yanada Reiko,
Obika Shingo,
Kobayashi Yusuke,
Inokuma Tsubasa,
Oyama Munetaka,
Yanada Kazuo,
Takemoto Yoshiji
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505147
Subject(s) - chemistry , stereoselectivity , palladium , catalysis , amide , tandem , indium , coupling reaction , combinatorial chemistry , cascade reaction , medicinal chemistry , stereochemistry , organic chemistry , materials science , composite material
The first efficient methods for the stereoselective synthesis of various ( E )‐, ( Z )‐, and disubstituted 3‐alkylideneoxindoles via radical cyclization reactions were investigated using tandem indium‐mediated carbometallation and palladium‐catalyzed cross‐coupling reactions. The proper combination of substrates and reaction conditions is important for good yields. The key step is the first stereoselective carboindation reaction using the strong coordination ability of an indium cation to the amide carbonyl oxygen. We applied this method to the synthesis of TMC‐95A precursor. A new N ‐debenzylation method with N ‐hydroxyphthalimide‐O 2 ‐Co(OAc) 2 ‐Mn(OAc) 2 was also developed using a one‐electron oxidation procedure.