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Catalysts 2019, 9(2), 192; https://doi.org/10.3390/catal9020192

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

Chair of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University in Toruń, 7 Gagarin Street, 87–100 Toruń, Poland
Received: 21 December 2018 / Revised: 12 February 2019 / Accepted: 12 February 2019 / Published: 20 February 2019
(This article belongs to the Special Issue Asymmetric Catalysis in Organic Synthesis)
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Abstract

A highly efficient and enantioselective approach to the synthesis of functionalized benzofuran-3(2H)-ones is presented. It proceeds via an intramolecular Stetter reaction using β,β-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(2H)-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. View Full-Text
Keywords: N-Heterocyclic carbenes; organocatalysis; Stetter reaction N-Heterocyclic carbenes; organocatalysis; Stetter reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Rafiński, Z. NHC-Catalyzed Organocatalytic Asymmetric Approach to 2,2-Disubstituted Benzofuran-3(2H)-ones Containing Fully Substituted Quaternary Stereogenic Center. Catalysts 2019, 9, 192.

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