期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 363, 期 15, 页码 3737-3743出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100261
关键词
Reductive rearrangement; 4H-Pyrans; Samarium powder; Zirconium tetrachloride; [1,2]-Aroxyl shift; Zinc
资金
- Russian Foundation for Basic Research [19-03-01024]
A variety of trans-2-acyl-2,3-dihydrofurans have been assembled and rearranged into annulated 4H-pyrans using Sm/TMSCl or Zn/ZrCl4 redox systems. The rearrangement involves SET reduction of carbonyl group to carbene followed by rare [1,2]-aroxyl shift. The use of Zn/ZrCl4 redox system enriched the synthetic toolbar.
A variety of trans-2-acyl-2,3-dihydrofurans have been assembled from readily available structurally diverse precursors and then rearranged into a series of annulated 4H-pyrans by the action of Sm/TMSCl or Zn/ZrCl4 redox systems. Present synthetic sequence is claimed as a modular approach to hetero- and carbon-fused 4H-pyrans. The rearrangement involves the SET reduction of carbonyl group to carbene followed by rare type of [1,2]-aroxyl shift. Synthetic toolbar was enriched with the use of the Zn/ZrCl4 redox system.
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