Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10259/6089
Título
Aldol–Tishchenko Reaction of α-Oxy Ketones: Diastereoselective Synthesis of 1,2,3-Triol Derivatives
Publicado en
Synthesis. 2021, V. 53, n. 20, p. 3725-3734
Editorial
Thieme
Fecha de publicación
2021-10
ISSN
0039-7881
DOI
10.1055/a-1509-5655
Résumé
α-Oxy ketones, easily accessible by conventional routes, can be selectively deprotonated generating an enolate intermediate, which upon treatment with paraformaldehyde undergoes an aldol–Tishchenko reaction, leading to relevant 1,2,3-triol fragments in a totally diastereoselective manner. The excellent stereocontrol in the generation of a quaternary stereocenter is attributed to stereoelectronic effects in the Evans intermediate. This methodology allows overcoming some limitations of our previously reported strategy, based on the reaction of α-lithiobenzyl ethers with esters and paraformaldehyde, broadening the scope of the obtained polyols. Synthetic applications of this process include the preparation of a new dilignol model and some functionalized oxetanes.
Palabras clave
aldol–Tishchenko reaction
enolates
α-oxy ketones
polyol derivatives
diastereoselectivity
oxetanes
Materia
Química orgánica
Chemistry, Organic
Versión del editor
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