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α,β-Unsaturated butenolides in an organocatalytic doubly annulative cascade for the preparation of 3,4-dihydrocoumarins

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Abstract

A new, organocatalytic doubly annulative cascade utilizing α,β-unsaturated butenolides and imines (derived from salicyl aldehydes and α-amino-γ-lactones) as starting materials is described. The developed strategy is based on two annulative processes: (1) initial [3 + 2]-dipolar cycloaddition allowing for the construction of a pyrrolidine ring; and (2) the butenolide-ring-opening reaction leading to the introduction of a 3,4-dihydrocoumarin framework. Target polycyclic compounds have been obtained with excellent chemical and stereochemical efficiencies.

Graphical abstract: α,β-Unsaturated butenolides in an organocatalytic doubly annulative cascade for the preparation of 3,4-dihydrocoumarins

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Publication details

The article was received on 10 Jan 2019, accepted on 05 Feb 2019 and first published on 05 Feb 2019


Article type: Communication
DOI: 10.1039/C9OB00068B
Citation: Org. Biomol. Chem., 2019, Advance Article

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    α,β-Unsaturated butenolides in an organocatalytic doubly annulative cascade for the preparation of 3,4-dihydrocoumarins

    D. Kowalczyk-Dworak and Ł. Albrecht, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00068B

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