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- Title
Organocatalytic Intramolecular [4+2] Cycloaddition between In Situ Generated Vinylidene ortho-Quinone Methides and Benzofurans.
- Authors
Wu, Xiaoyan; Xue, Lu; Li, Dongmei; Jia, Shiqi; Ao, Jun; Deng, Jun; Yan, Hailong
- Abstract
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.
- Subjects
ORGANOCATALYSIS; RING formation (Chemistry); VINYLIDENE compounds; QUINONE methides; BENZOFURANS
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 44, p13910
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201707523