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Can a Ketone Be More Reactive than an Aldehyde? Catalytic Asymmetric Synthesis of Substituted Tetrahydrofurans

MPS-Authors
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Lee,  Sunggi
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Bae,  Han Yong
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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Lee, Bae, List 2018.pdf
(Postprint), 676KB

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Citation

Lee, S., Bae, H. Y., & List, B. (2018). Can a Ketone Be More Reactive than an Aldehyde? Catalytic Asymmetric Synthesis of Substituted Tetrahydrofurans. Angewandte Chemie International Edition, 57(37), 12162-12166. doi:10.1002/anie.201806312.


Cite as: http://hdl.handle.net/21.11116/0000-0002-16A3-D
Abstract
O‐heterocycles bearing tetrasubstituted stereogenic centers are prepared via catalytic chemo‐ and enantioselective nucleophilic additions to ketoaldehydes, in which the ketone reacts preferentially over the aldehyde. Five‐ and six‐membered rings with both aromatic and aliphatic substituents, as well as an alkynyl substituent, are obtained. Moreover, 2,2,5‐trisubstituted and 2,2,5,5‐tetrasubstituted tetrahydrofurans are synthesized with excellent stereoselectivities. Additionally, the synthetic utility of the described method is demonstrated with a three‐step synthesis of the side chain of anhydroharringtonine.