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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