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Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes

MPS-Authors
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Liu,  Luping
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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

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

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Kaib,  Philip S. J.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Goddard,  Richard
Service Department Lehmann (EMR), 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

Liu, L., Kim, H., Xie, Y., Farès, C., Kaib, P. S. J., Goddard, R., et al. (2017). Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes. Journal of the American Chemical Society, 139(39), 13656-13659. doi:10.1021/jacs.7b08357.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002E-10B6-C
Abstract
Despite its significant potential, a general catalytic asymmetric [4+2]-cycloaddition of simple and electronically unbiased dienes with any type of aldehyde has long been unknown. Previously developed methodologies invariably require activated, electronically engineered substrates. We now provide a general solution to this problem. We show that highly acidic and confined imidodiphosphorimidates (IDPis) are extremely effective Brønsted acid catalysts of the hetero-Diels–Alder reaction of a wide variety of aldehydes and dienes to give enantiomerically enriched dihydropyrans. Excellent stereoselectivity is generally observed and a variety of scents and natural products can be easily accessed.