2024-03-28T15:37:16Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/60892022-10-31T23:42:08Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
Aldol–Tishchenko Reaction of α-Oxy Ketones: Diastereoselective Synthesis of 1,2,3-Triol Derivatives
Sedano Labrador, Carlos
Virumbrales Ortiz, Cintia
Suarez Pantiga, Samuel
Sanz Díez, Roberto
aldol–Tishchenko reaction
enolates
α-oxy ketones
polyol derivatives
diastereoselectivity
oxetanes
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.
2021-11-04
2021-11-04
2021-10
info:eu-repo/semantics/article
0039-7881
http://hdl.handle.net/10259/6089
10.1055/a-1509-5655
eng
Synthesis. 2021, V. 53, n. 20, p. 3725-3734
https://doi.org/10.1055/a-1509-5655
info:eu-repo/semantics/openAccess
Thieme