Issue 17, 2019

Decarboxylative, trienamine mediated cycloaddition for the synthesis of 3,4-dihydrocoumarin derivatives

Abstract

In this Communication, a new approach for trienamine chemistry is described. It is based on the application of carboxylic-acid-activated dienophiles that undergo spontaneous decarboxylative protonation after the initial [4 + 2]-cycloaddition step. The utilization of such a novel cascade reaction for the synthesis of biologically relevant 3,4-dihydrocoumarins has been demonstrated. High levels of enantiocontrol and excellent yield of the cascade reaction have been achieved by the use of diphenylprolinol diphenylmethylsilyl ether.

Graphical abstract: Decarboxylative, trienamine mediated cycloaddition for the synthesis of 3,4-dihydrocoumarin derivatives

Supplementary files

Article information

Article type
Communication
Submitted
16 Feb 2019
Accepted
28 Mar 2019
First published
29 Mar 2019

Org. Biomol. Chem., 2019,17, 4238-4242

Decarboxylative, trienamine mediated cycloaddition for the synthesis of 3,4-dihydrocoumarin derivatives

A. Albrecht, J. Bojanowski, A. Kot and L. Sieroń, Org. Biomol. Chem., 2019, 17, 4238 DOI: 10.1039/C9OB00386J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements