Synthesis of a Simplified Version of Stable Bulky and Rigid Cyclic (Alkyl)(amino)carbenes, and Catalytic Activity of the Ensuing Gold(I) Complex in the Three-Component Preparation of 1,2-Dihydroquinoline Derivatives
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 prov...
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| Veröffentlicht in: | Journal of the American Chemical Society 2009-06, Vol.131 (24), p.8690-8696 |
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| creator | Zeng, Xiaoming Frey, Guido D Kinjo, Rei Donnadieu, Bruno Bertrand, Guy |
| description | 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. |
| doi_str_mv | 10.1021/ja902051m |
| format | Article |
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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. 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| ispartof | Journal of the American Chemical Society, 2009-06, Vol.131 (24), p.8690-8696 |
| issn | 0002-7863 1520-5126 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Aldehydes - chemistry Alkynes - chemistry Amines - chemistry Catalysis Cyclohexenes - chemistry Gold - chemistry Magnetic Resonance Spectroscopy Methane - analogs & derivatives Methane - chemical synthesis Methane - chemistry Models, Molecular Organometallic Compounds - chemistry Quinolines - chemical synthesis |
| title | Synthesis of a Simplified Version of Stable Bulky and Rigid Cyclic (Alkyl)(amino)carbenes, and Catalytic Activity of the Ensuing Gold(I) Complex in the Three-Component Preparation of 1,2-Dihydroquinoline Derivatives |
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