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A General Catalytic Asymmetric Prins Cyclization

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

/persons/resource/persons58764

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

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Citation

Liu, L., Kaib, P. S. J., Tap, A., & List, B. (2016). A General Catalytic Asymmetric Prins Cyclization. Journal of the American Chemical Society, 138(34), 10822-10825. doi:10.1021/jacs.6b07240.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002B-43B1-D
Abstract
A new class of highly acidic confined imino-imidodiphosphate (iIDP) Brønsted acids catalyze the asymmetric Prins cyclization of both aliphatic and aromatic aldehydes. Diverse functionalized 4-methylenetetrahydropyrans are obtained in good to excellent yields and with good to excellent regio- and enantioselectivities. Our iIDP catalysts provide an efficient and scalable enantioselective approach to various fragrances, including rose oxide and doremox.