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Scalable and Highly Diastereo- and Enantioselective Catalytic Diels−Alder Reaction of α,β - Unsaturated Methyl Esters

MPS-Authors
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Gatzenmeier,  Tim
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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Yepes,  Diana
Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons191820

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

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Neese,  Frank
Research Department Neese, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Bistoni,  Giovanni
Research Group Bistoni, 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

Gatzenmeier, T., Turberg, M., Yepes, D., Xie, Y., Neese, F., Bistoni, G., et al. (2018). Scalable and Highly Diastereo- and Enantioselective Catalytic Diels−Alder Reaction of α,β - Unsaturated Methyl Esters. Journal of the American Chemical Society, 140(40), 12671-12676. doi:10.1021/jacs.8b07092.


Cite as: https://hdl.handle.net/21.11116/0000-0002-57A0-7
Abstract
Despite tremendous advances in enantioselective catalysis of the Diels−Alder reaction, the use of simple α,β-unsaturated esters, one of the most abundant and useful class of dienophiles, is still severely limited in scope due to their low reactivity. We report here a catalytic asymmetric Diels−Alder methodology for a large
variety of α,β-unsaturated methyl esters and different dienes based on extremely reactive silylium imidodiphos-phorimidate (IDPi) Lewis acids. Mechanistic insights from accurate domain-based local pair natural orbital coupled-cluster (DLPNO-CCSD(T)) calculations rationalize the catalyst control and stereochemical outcome.