期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 24, 页码 8690-8696出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja902051m
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资金
- NIH [R01 GM 68825]
- China Scholarship Council
- Alexander von Humboldt Foundation
- Japanese Society for Promotion of Science
A 95/5 mixture of cis and trans 2,4-dimethyl-3-cyclohexenecarboxaldehyde (trivertal), a common fragrance and flavor material produced in bulk quantities, serves as the precursor for the synthesis of a stable spirocyclic (alkyl)(amino)carbene, in which the 2-methyl-substituted cyclohexenyl group provides steric protection to an ensuing metal. The efficiency of this carbene as ligand for transition metal based catalysts is first illustrated by the gold(I) catalyzed hydroamination of internal alkynes with secondary dialkyl amines, a process with little precedent. The feasibility of this reaction allows for significantly enlarging the scope of the one-pot three-component synthesis of 1,2-dihydroquinoline derivatives, and related nitrogen-containing heterocycles. Indeed, two different alkynes were used, which include an internal alkyne for the first step.
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