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Issue 4, 2015
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Organocatalytic oxa-Diels–Alder reaction of α,β-unsaturated ketones under non-classical conditions

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Abstract

Non-classical reaction conditions are compatible with organocatalysis and can often improve reaction course. Oxa-Diels–Alder reaction of acyclic α,β-unsaturated ketones with aldehydes is a challenging transformation that affords valuable pyranone products. Application of microwave irradiation and solvent-free conditions during ball-milling had the best influence on this reaction, in terms of shortened reaction times and increased product yields. Other factors, such as aqueous conditions, ultrasound and flow conditions also bring notable improvements. Unfortunately, a range of chiral organocatalysts provided only small enantioselectivity of the reaction of up to e.r. 63 : 37.

Graphical abstract: Organocatalytic oxa-Diels–Alder reaction of α,β-unsaturated ketones under non-classical conditions

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Supplementary files

Article information


Submitted
20 Dec 2014
Accepted
09 Jan 2015
First published
09 Jan 2015

New J. Chem., 2015,39, 2573-2579
Article type
Paper
Author version available

Organocatalytic oxa-Diels–Alder reaction of α,β-unsaturated ketones under non-classical conditions

M. Mojzesová, M. Mečiarová, R. Marti and R. Šebesta, New J. Chem., 2015, 39, 2573
DOI: 10.1039/C4NJ02361G

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