期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 10, 页码 3756-3759出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja312346s
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资金
- National Research Foundation Singapore [NRF-RF-2009-05]
- Nanyang Technological University
We describe here a [3+3]-type condensation reaction of O-acetyl ketoximes and alpha,beta-unsaturated aldehydes that is synergistically catalyzed by a copper(I) salt and a secondary ammonium salt (or amine). This redox-neutral reaction allows modular synthesis of a variety of substituted pyridines under mild conditions with tolerance of a broad range of functional groups. The reaction is driven by a merger of iminium catalysis and redox activity of the copper catalyst, which would initially reduce the oxime N-O bond to generate a nucleophilic copper(II) enamide and later oxidize a dihydropyridine intermediate to the pyridine product.
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