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Issue 45, 2017
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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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Article information


Submitted
25 Sep 2017
Accepted
04 Oct 2017
First published
04 Oct 2017

Org. Biomol. Chem., 2017,15, 9566-9569
Article type
Communication

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, 15, 9566
DOI: 10.1039/C7OB02397A

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