期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 44, 页码 13722-13726出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201707523
关键词
cycloaddition; heterocycles; organocatalysis; polycycles; rearrangements
资金
- Fundamental Research Funds for the Central Universities in China [CQDXWL-2014-Z003]
- Scientific Research Foundation of China [21402016]
- Graduate Scientific Research and Innovation Foundation of Chongqing, China [CYS17044, CYB16032]
Described herein is the enantioselective construction of oxygen-containing [5-6-5] tricyclic heterocycles by an organocatalyzed asymmetric [4+2] cycloaddition of vinylidene ortho-quinone methides and benzofurans. According to this methodology, a series of oxygen-containing [5-6-5] tricyclic heterocycles with various functional groups were synthesized in excellent enantio-and diastereoselectivities (>99% ee, >20:1 d.r.). Furthermore, the deuterium-labeling experiments and high-resolution mass spectroscopy demonstrated that a vinylidene ortho-quinone methide intermediate was involved and possibly resulted from a prototropic rearrangement of 2-ethynylphenol. Remarkably, a catalyst loading as low as 0.1 mol%, and a gram-scale synthesis were achieved for this transformation.
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