Jump to main content
Jump to site search

Issue 8, 2018
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
11 Dec 2017
Accepted
24 Jan 2018
First published
24 Jan 2018

Org. Biomol. Chem., 2018,16, 1277-1286
Article type
Paper

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

Social activity

Search articles by author

Spotlight

Advertisements