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Confined Acid-Catalyzed Asymmetric Carbonyl-Ene Cyclization

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

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

/persons/resource/persons186078

Zheng,  Yiying
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58388

Alachraf,  Mohammed Wasim
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Thiel,  Walter
Research Department List, 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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Supplementary Material (public)

ja5b09484_si_001.pdf
(Supplementary material), 533KB

ja5b09484_si_003.pdf
(Supplementary material), 3MB

Citation

Liu, L., Leutzsch, M., Zheng, Y., Alachraf, M. W., Thiel, W., & List, B. (2015). Confined Acid-Catalyzed Asymmetric Carbonyl-Ene Cyclization. Journal of the American Chemical Society, 137(41), 13268-13271. doi:10.1021/jacs.5b09484.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0029-2E68-3
Abstract
A highly enantioselective Brønsted acid catalyzed intramolecular carbonyl–ene reaction of olefinic aldehydes has been developed. Using a confined imidodiphosphate catalyst, the reaction delivers diverse trans-3,4-disubstituted carbo- and heterocyclic five-membered rings in high yields and with good to excellent diastereo- and enantioselectivities. ESI-MS, NMR, and DFT mechanistic studies reveal that the reaction proceeds via a stepwise pathway involving a novel covalent intermediate.