Asymmetric Synthesis of Amines through Rhodium-Catalyzed C–H Amination with Sulfonimidoylnitrenes

Abstract An efficient asymmetric C–H amination of benzylic and allylic substrates, as well as of adamantane derivatives, through catalytic C–H insertion of a chiral nitrene is reported. The reaction involves a chiral rhodium(II) complex, an iodine(III) oxidant, and a sulfonimid­amide as a nitrene pr...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2013-08, Vol.45 (15), p.2079-2087
Main Authors: Darses, Benjamin, Jarvis, Amanda G., Mafroud, Abdel-Kader, Estenne-Bouhtou, Geneviève, Dargazanli, Gihad, Dauban, Philippe
Format: Article
Language:English
Subjects:
Catalysis
Chemical Sciences
Organic chemistry
practical synthetic procedures
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Summary:Abstract An efficient asymmetric C–H amination of benzylic and allylic substrates, as well as of adamantane derivatives, through catalytic C–H insertion of a chiral nitrene is reported. The reaction involves a chiral rhodium(II) complex, an iodine(III) oxidant, and a sulfonimid­amide as a nitrene precursor. Experimental protocols for the preparation of the reagents and the catalytic nitrene are provided. The C–H amination can provide the corresponding amino derivatives on a gram scale. Various methods for the cleavage of the sulfonimidoyl group to give the corresponding tert -butoxycarbonyl- or acetyl-protected optically pure amines are also described.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0033-1339280