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An asymmetric multicatalytic reaction sequence of 2-hydroxycinnamaldehydes and enolic 1,3-dicarbonyl compounds to construct bridged bicyclic acetals

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Abstract

An efficient asymmetric multicatalytic system involving iminium catalysis and anion-binding catalysis has been developed, which exhibited high catalytic activity in a one-pot, two-step reaction sequence of 2-hydroxycinnamaldehydes and enolic 1,3-dicarbonyl nucleophiles to construct an enantioenriched 2,8-dioxabicyclo[3.3.1]nonane scaffold. The inherent phenolic hydroxyl group of 2-hydroxycinnamaldehyde played an important role in the catalytic process, which potentially provided a phenoxide anion to combine with the thiourea moiety of a bifunctional tertiary amine-thiourea catalyst via anion binding, thus making the developed multicatalytic system more economic and different from the previously reported catalytic mode.

Graphical abstract: An asymmetric multicatalytic reaction sequence of 2-hydroxycinnamaldehydes and enolic 1,3-dicarbonyl compounds to construct bridged bicyclic acetals

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Publication details

The article was received on 17 Oct 2019, accepted on 28 Nov 2019 and first published on 02 Dec 2019


Article type: Research Article
DOI: 10.1039/C9QO01272A
Org. Chem. Front., 2020, Advance Article

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    An asymmetric multicatalytic reaction sequence of 2-hydroxycinnamaldehydes and enolic 1,3-dicarbonyl compounds to construct bridged bicyclic acetals

    X. Zhang, X. Lv, J. Pei, R. Tan and Y. Liu, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01272A

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