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Brønsted-base-catalyzed remote cascade reactivity of 2,4-dienones – asymmetric synthesis of tetrahydrothiophenes

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Abstract

This study demonstrates that the remote cascade functionalization of 2,4-dienones can be realized by employing Brønsted base catalysis. The developed cascade involving 1,6-addition followed by the intramolecular aldol reaction provides a straightforward access to polysubstituted tetrahydrothiophene derivatives of biological and synthetic importance. Target products, bearing three contiguous stereocenters including one quaternary, have been obtained with excellent yields (up to 98%) and with good to high stereocontrol (>20 : 1 dr, up to 97 : 3 er) with the reaction cascade being promoted by a simple and readily available cinchona alkaloid cinchonine.

Graphical abstract: Brønsted-base-catalyzed remote cascade reactivity of 2,4-dienones – asymmetric synthesis of tetrahydrothiophenes

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Publication details

The article was received on 25 Sep 2017, accepted on 04 Oct 2017 and first published on 04 Oct 2017


Article type: Communication
DOI: 10.1039/C7OB02397A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Brønsted-base-catalyzed remote cascade reactivity of 2,4-dienones – asymmetric synthesis of tetrahydrothiophenes

    A. Przydacz, R. Kowalczyk and Ł. Albrecht, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02397A

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