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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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Publication details

The article was received on 20 Dec 2014, accepted on 09 Jan 2015 and first published on 09 Jan 2015


Article type: Paper
DOI: 10.1039/C4NJ02361G
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Citation: New J. Chem., 2015,39, 2573-2579
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    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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