期刊
CHEMICAL SCIENCE
卷 10, 期 1, 页码 83-89出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc03434f
关键词
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资金
- Royal Society
- AstraZeneca
- EPSRC [EP/N031792/1]
- Herchel Smith Foundation
- Higher Education Funding Council for England
- EPSRC [EP/N031792/1] Funding Source: UKRI
The study of a selective palladium(ii)-catalyzed C(sp(3))-H acetoxylation reaction on a class of cyclic alkyl amines is reported. Computational modelling and kinetic studies were used to provide support for a mechanism involving selective C-O bond formation from a -aminoalkyl-Pd(iv) intermediate. The C-O bond forming step was computed to occur by a dissociative ionization mechanism followed by an S(N)2 process involving external acetate attack at the C-Pd(iv) bond. This pathway was computed to be of lowest energy with no competing C-N products observed. Additionally, with a few modifications to reaction conditions, preliminary studies showed that this process could be rendered enantioselective in the presence of a non-racemic BINOL-phosphoric acid.
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