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...

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Published inOrganic & biomolecular chemistry Vol. 16; no. 8; pp. 1277 - 1286
Main Authors Becerra-Figueroa, L., Movilla, S., Prunet, J., Miscione, G. P., Gamba-Sanchez, D.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.02.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DENSITY FUNCTIONALS
ALCOHOLS
DIASTEREOSELECTIVE SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
THERMOCHEMICAL KINETICS
EFFICIENT PROCEDURE
DEHYDROAMINO ACIDS
ALDEHYDES
PROTECTED SYN 1,3-DIOLS
CONJUGATE ADDITION
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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