RT info:eu-repo/semantics/article
T1 Aldol–Tishchenko Reaction of α-Oxy Ketones: Diastereoselective Synthesis of 1,2,3-Triol Derivatives
A1 Sedano Labrador, Carlos
A1 Virumbrales Ortiz, Cintia
A1 Suárez Pantiga, Samuel
A1 Sanz Díez, Roberto
K1 aldol–Tishchenko reaction
K1 enolates
K1 α-oxy ketones
K1 polyol derivatives
K1 diastereoselectivity
K1 oxetanes
K1 Química orgánica
K1 Chemistry, Organic
AB 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.
PB Thieme
SN 0039-7881
YR 2021
FD 2021-10
LK http://hdl.handle.net/10259/6089
UL http://hdl.handle.net/10259/6089
LA eng
NO Ministerio de Ciencia e Innovación andFEDER (CTQ2016-75023-C2-1-P), and Junta de Castilla y León and FEDER(BU291P18, BU049P20). The project leading to these results has alsoreceived funding from the “la Caixa” Foundation, under agreementLCF/PR/PR18/51130007) (CAIXA-UBU001). A postdoctoral contract(S.S.-P.) and a predoctoral contract (C.S.) were funded by Junta de Castillay León and FEDER and Ministerio de Educación (FPU), respectively
DS Repositorio Institucional de la Universidad de Burgos
RD 24-nov-2024