Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 33, Pages 14096-14100Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202005313
Keywords
[8+2] cycloaddition; medium-sized ring; palladium catalysis; visible light
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Funding
- National Science Foundation of China [21822103, 21820102003, 21822303, 21772052, 21772053, 91956201]
- Program of Introducing Talents of Discipline to Universities of China (111 Program) [B17019]
- Natural Science Foundation of Hubei Province [2017AHB047]
- International Joint Research Center for Intelligent Biosensing Technology and Health
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Higher-order cycloadditions, particularly [8+2] cycloadditions, are a straightforward and efficient strategy for constructing significant medium-sized architectures. Typically, configuration-restrained conjugated systems are utilized as 8 pi-components for higher-order concerted cycloadditions. However, for this reason, 10-membered monocyclic skeletons have never been constructed via catalytic asymmetric [8+2] cycloaddition with high peri- and stereoselectivity. Here, we accomplished an enantioselective [8+2] dipolar cycloaddition via the merger of visible-light activation and asymmetric palladium catalysis. This protocol provides a new route to 10-membered monocyclic architectures bearing chiral quaternary stereocenters with high chemo-, peri-, and enantioselectivity. The success of this strategy relied on the facile in situ generation of Pd-containing 1,8-dipoles and their enantioselective trapping by ketene dipolarophiles, which were formed in situ via a photo-Wolff rearrangement.
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