期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 17, 页码 6577-6579出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo0708137
关键词
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The cyclization of amino-alkynes 1 in which an amino group is attached to the aromatic ring, proceeded smoothly using a catalytic amount of Pd(PPh3)(4) and benzoic acid in toluene at 120 degrees C, leading to the formation of the 2-substituted tetrahydroquinolines 2. An asymmetric variant of the reaction using the chiral palladium catalyst (prepared in situ by mixing Pd-2(dba)(3)center dot CHCl3 and (R,R)-RENORPHOS) was also explored. The absolute configuration of the enantiomerically enriched tetrahydroquinolines, obtained in this way, was determined by converting them to the known compounds and was found to be R. The alkaloids such as (+/-)-galipinine, (+/-)-angustureine, arid their optically active form were synthesized by using this reaction as a key step.
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