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A solid noncovalent organic double-helix framework catalyzes asymmetric [6 + 4] cycloaddition

MPS-Authors
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Zheng,  Tianyu
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Nöthling,  Nils
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wang,  Zikuan
Research Group Manganas, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Mitschke,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leutzsch,  Markus
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Zheng, T., Nöthling, N., Wang, Z., Mitschke, B., Leutzsch, M., & List, B. (2024). A solid noncovalent organic double-helix framework catalyzes asymmetric [6 + 4] cycloaddition. Science, 385(6710), 765-770. doi:10.1126/science.adp1127.


Cite as: https://hdl.handle.net/21.11116/0000-000F-BA8B-3
Abstract
Whereas [4 + 2] cycloadditions are among the most powerful tools in the chemist’s synthetic arsenal, controlling reactivity and selectivity of [6 + 4] cycloadditions has proven to be extremely challenging. Such transformations, especially if compatible with simple hydrocarbon-based substrates, could ultimately provide a general approach to highly valuable and otherwise difficult to access 10-membered rings. We report here that highly acidic and confined imidodiphosphorimidate catalysts do not catalyze this reaction under homogeneous conditions. Notably, however, they can spontaneously precipitate an insoluble and double helix–shaped noncovalent organic framework, which acts as a distinctively reactive and stereoselective catalyst of [6 + 4] cycloadditions of simple dienes with tropone.