Issue 8, 2020

Asymmetric pyrone Diels–Alder reactions enabled by dienamine catalysis

Abstract

Despite the proven value in utilizing pyrone dienes to create molecular complexity via Diels–Alder reactions with varied dienophiles, few examples of effective catalytic, asymmetric variants of this process have been developed. Herein, we show that the use of Jørgensen–Hayashi-type catalysts can convert an array of α,β-unsaturated aldehydes into chiral dienamines that can formally add in a Diels–Alder fashion to a number of electron-deficient pyrones of the coumalate-type to generate optically active [2.2.2]-bicyclic lactones. In most cases, the reactions proceed with good to excellent diastereo- and enantiocontrol (up to 99% ee). Models to explain that stereoselectivity, as well as several additional transformations of the resultant products, are also presented.

Graphical abstract: Asymmetric pyrone Diels–Alder reactions enabled by dienamine catalysis

Supplementary files

Article information

Article type
Edge Article
Submitted
12 Nov 2019
Accepted
23 Dec 2019
First published
26 Dec 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 2175-2180

Asymmetric pyrone Diels–Alder reactions enabled by dienamine catalysis

C. J. F. Cole, L. Fuentes and S. A. Snyder, Chem. Sci., 2020, 11, 2175 DOI: 10.1039/C9SC05738B

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