Unusual product formation in tungsten(0)-catalysed reactions of propargylic alcohols and secondary amines: Hydroamination and the construction of the tetrahydrofuran ring

Add time:07/27/2019    Source:sciencedirect.com

In reactions of propargylic alcohols, RH(HO)CCCH (prop-2-yn-1-ol, meso-but-3-yn-2-ol), with secondary cyclic amines (piperidine, pyrrolidine, morpholine, 1-methylpiperazine, 4-methylpiperidine and meso-3,5-dimethylpiperidine), catalysed by cis-[W(CO)4(pip)2], previously unknown diamines containing the tetrahydrofuran ring were isolated in relatively good yield, up to 80%, identified by GC–MS, and characterized by NMR spectroscopy. The new structures were studied by DFT: the 1H and 13C chemical shifts were calculated and compared with those observed experimentally.

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