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

Becerra-Figueroa, L., Movilla, S., Prunet, J. , Miscione, G. P. and Gamba-Sánchez, D. (2018) An intramolecular oxa-Michael reaction on α,β-unsaturated α-amino-δ-hydroxycarboxylic acid esters. Synthesis of functionalized 1,3-dioxanes. Organic and Biomolecular Chemistry, 16(8), pp. 1277-1286. (doi:10.1039/c7ob03066e) (PMID:29384169)

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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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Prunet, Dr Joelle
Authors: Becerra-Figueroa, L., Movilla, S., Prunet, J., Miscione, G. P., and Gamba-Sánchez, D.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic and Biomolecular Chemistry
Publisher:Royal Society of Chemistry
ISSN:1477-0520
ISSN (Online):1477-0539
Published Online:24 January 2018
Copyright Holders:Copyright © 2018 The Royal Society of Chemistry
First Published:First published in Organic and Biomolecular Chemistry 16(8): 1277-1286
Publisher Policy:Reproduced in accordance with the publisher copyright policy

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