Heck‐Type Cyclization of Oxime Ethers: Stereoselective Carbon–Carbon Bond Formation with Aryl Halides To Produce Heterocyclic Oximes | Zendy

Ohno Hiroaki | Zendy; Aso Akimasa | Zendy; Kadoh Yoichi | Zendy; Fujii Nobutaka | Zendy; Tanaka Tetsuaki | Zendy

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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.

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