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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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Article information


Submitted
17 Oct 2019
Accepted
28 Nov 2019
First published
02 Dec 2019

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

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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