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Heck‐Type Cyclization of Oxime Ethers: Stereoselective Carbon–Carbon Bond Formation with Aryl Halides To Produce Heterocyclic Oximes
Author(s) -
Ohno Hiroaki,
Aso Akimasa,
Kadoh Yoichi,
Fujii Nobutaka,
Tanaka Tetsuaki
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701868
Subject(s) - chemistry , moiety , aryl , halide , oxime , alkyl , stereoselectivity , indole test , medicinal chemistry , benzofuran , organic chemistry , palladium , heck reaction , catalysis
Irrespective of the isomeric ratio of the starting material, the palladium‐catalyzed cyclization of oxime ethers with an aryl halide moiety proceeds in a highly Z ‐selective manner to give indolin‐3‐one O ‐alkyl oximes in good yields (see scheme). The reaction is also applicable to the construction of benzofuran‐3‐one and fused‐indole frameworks. R 1 =H, Me, OMe, CO 2 Me; R 2 =Me, benzyl; Ts= p ‐toluenesulfonyl.