An intramolecular oxa-Michael reaction on a, β-unsaturated α-amino-δ-hydroxycarboxylic acid esters. Synthesis of functionalized 1,3-dioxanes
A highly diastereoselective intramolecular oxa-Michael reaction on alpha,beta-unsaturated alpha-aminod-delta-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...
Saved in:
Published in | Organic & biomolecular chemistry Vol. 16; no. 8; pp. 1277 - 1286 |
---|---|
Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
CAMBRIDGE
Royal Soc Chemistry
28.02.2018
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | A highly diastereoselective intramolecular oxa-Michael reaction on alpha,beta-unsaturated alpha-aminod-delta-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. |
---|---|
ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/c7ob03066e |