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Decarboxylation-promoted Pd-catalyzed asymmetric propargylic [3 + 2] annulation for the enantioselective construction of a quaternary stereocenter in 2,3-dihydrofurans

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Abstract

The enantioselective construction of a quaternary stereocenter in 2,3-dihydrofuran frameworks has been realized via the palladium-catalyzed asymmetric [3 + 2] cycloaddition of tertiary propargylic carbonates with β-ketoesters enabled by a chiral ferrocene/benzimidazole-based bidentate P,N-ligand. The reaction was significantly promoted by loss of CO2 to irreversibly form π-propargylpalladium or allenylpalladium intermediates. This protocol features a good tolerance of functional groups in both tertiary propargylic carbonates and β-ketoesters, thereby delivering a variety of highly functionalized chiral 2,3-dihydrofurans bearing a quaternary stereocenter at the 2-position and an exocyclic double bond at the 3-position in good chemical yields and high enantioselectivities (up to 98% ee).

Graphical abstract: Decarboxylation-promoted Pd-catalyzed asymmetric propargylic [3 + 2] annulation for the enantioselective construction of a quaternary stereocenter in 2,3-dihydrofurans

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Publication details

The article was received on 13 Nov 2017, accepted on 29 Dec 2017 and first published on 02 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB02778H
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Decarboxylation-promoted Pd-catalyzed asymmetric propargylic [3 + 2] annulation for the enantioselective construction of a quaternary stereocenter in 2,3-dihydrofurans

    K. Li, F. Zhu, Z. Liu, J. Tong and X. Hu, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02778H

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