NHC-Catalyzed Organocatalytic Asymmetric Approach to 2,2-Disubstituted Benzofuran-3(2<i>H</i>)-ones Containing Fully Substituted Quaternary Stereogenic Center

A highly efficient and enantioselective approach to the synthesis of functionalized benzofuran-3(2<i>H</i>)-ones is presented. It proceeds via an intramolecular Stetter reaction using &#946;,&#946;-disubstituted Michael acceptors in the construction of five-membered rings with fu...

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Bibliographic Details
Main Author: Zbigniew Rafiński
Format: Article
Language:English
Published: MDPI AG 2019-02-01
Series:Catalysts
Subjects:
Online Access:https://www.mdpi.com/2073-4344/9/2/192
Description
Summary:A highly efficient and enantioselective approach to the synthesis of functionalized benzofuran-3(2<i>H</i>)-ones is presented. It proceeds via an intramolecular Stetter reaction using &#946;,&#946;-disubstituted Michael acceptors in the construction of five-membered rings with fully-substituted quaternary stereogenic centers and is promoted by terpene-derived triazolium salts. As a result, a series of chiral 2,2-disubstituted benzofuran-3(2<i>H</i>)-one derivatives with linear, branched, and cyclic aliphatic substitutions on the quaternary stereogenic center were obtained in high yields and with excellent enantioselectivities of up to 99% ee.
ISSN:2073-4344