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

文献情報

出版日 2017-10-04

DOI 10.1039/C7OB02397A

インパクトファクター 3.876

著者

Artur Przydacz, Rafał Kowalczyk, Łukasz Albrecht

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要旨

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.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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

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