Abstract
Copper-catalyzed cross-coupling between (S)-S-methyl-S-phenylsulfoximine (1) and 2-iodobenzonitrile (2) resulted in the discovery of an unprecedented one-pot triple arylation sequence to give (R)-(−)-2-[(5-oxido-5-phenyl-5λ4-isoquino[4,3-c][2,1]benzothiazin- 12-yl)amino]benzonitrile (4). Here, we describe the synthesis of the title compound (R)-4 and the elucidation of its structure by means of various techniques.
Highlights
Functionalized sulfoximines derived from (S)-S-methyl-S-phenylsulfoximine (1) are efficient chiral ligands in asymmetric metal catalysis [1,2,3,4,5,6]
Syntheses of (S)- and (R)-3 had only been achieved by palladium-catalyzed cross-couplings of the corresponding enantiopure sulfoximine 1 with
It was envisaged to utilize a coppercatalyzed protocol [10] for the preparation of (S)-3 starting from 2-iodobenzonitrile (2). Application of this copper-based system furnished a novel compound [(R)-(−)-2-[(5oxido-5-phenyl-5λ4-isoquino[4,3-c][2,1]benzothiazin-12-yl)amino]benzonitrile (4)], which was formed by an unexpected triple arylation cascade with aryl iodide 2 under these conditions
Summary
Functionalized sulfoximines derived from (S)-S-methyl-S-phenylsulfoximine (1) are efficient chiral ligands in asymmetric metal catalysis [1,2,3,4,5,6]. Application of this copper-based system furnished a novel compound [(R)-(−)-2-[(5oxido-5-phenyl-5λ4-isoquino[4,3-c][2,1]benzothiazin-12-yl)amino]benzonitrile (4)], which was formed by an unexpected triple arylation cascade with aryl iodide 2 under these conditions. Arylation product (S)-3 was only obtained in 61% yield and a considerable amount (23%) of an unknown second compound was isolated.
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