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Issue 8, 2018
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An intramolecular oxa-Michael reaction on α,β-unsaturated α-amino-δ-hydroxycarboxylic acid esters. Synthesis of functionalized 1,3-dioxanes

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Abstract

A highly diastereoselective intramolecular oxa-Michael reaction on α,β-unsaturated α-amino-δ-hydroxycarboxylic acid esters is presented; 1,3-dioxanes functionalized in positions 2,4 and 6 were obtained in good yields and with excellent selectivities; an experimental and computational study was carried out to understand the reaction course in terms of yields and selectivities. This reaction proceeds under mild reaction conditions using highly electrophilic aldehydes and ketones.

Graphical abstract: An intramolecular oxa-Michael reaction on α,β-unsaturated α-amino-δ-hydroxycarboxylic acid esters. Synthesis of functionalized 1,3-dioxanes

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Publication details

The article was received on 11 Dec 2017, accepted on 24 Jan 2018 and first published on 24 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB03066E
Citation: Org. Biomol. Chem., 2018,16, 1277-1286
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    An intramolecular oxa-Michael reaction on α,β-unsaturated α-amino-δ-hydroxycarboxylic acid esters. Synthesis of functionalized 1,3-dioxanes

    L. Becerra-Figueroa, S. Movilla, J. Prunet, G. P. Miscione and D. Gamba-Sánchez, Org. Biomol. Chem., 2018, 16, 1277
    DOI: 10.1039/C7OB03066E

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