Issue 10, 2019

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

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

Supplementary files

Article information

Article type
Communication
Submitted
10 Jan 2019
Accepted
05 Feb 2019
First published
05 Feb 2019

Org. Biomol. Chem., 2019,17, 2624-2628

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, 17, 2624 DOI: 10.1039/C9OB00068B

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