RT info:eu-repo/semantics/article
T1 Merging α-Lithiation and Aldol-Tishchenko Reaction to Construct Polyols from Benzyl Ethers
A1 Sedano Labrador, Carlos
A1 Velasco, Rocío
A1 Suárez Pantiga, Samuel
A1 Sanz Díez, Roberto
K1 Reaction products
K1 Aldehydes
K1 Ethers
K1 Pharmaceuticals
K1 Aldol reactions
K1 Química orgánica
K1 Chemistry, Organic
AB α-Lithiobenzyl ethers, generated by selective α-lithiation, undergo an aldol-Tishchenko reaction upon treatment with carboxylic esters and paraformaldehyde. The reaction of the organolithium with the carboxylate generates an intermediate enolate that, after formaldehyde addition, affords 1,2,3-triol derivatives in a straightforward and one-pot manner. These products are obtained as single diastereoisomers bearing a quaternary stereocenter. The complete diastereocontrol of the aldol-Tishchenko process is attributed to stereoelectronic preferences in the transition state.
PB American Chemical Society
SN 1523-7060
YR 2020
FD 2020-10
LK http://hdl.handle.net/10259/5535
UL http://hdl.handle.net/10259/5535
LA eng
NO Ministerio de Ciencia e Innovación and FEDER (CTQ2016-75023-C2-1-P) and Junta de Castilla y León and FEDER (BU291P18)
DS Repositorio Institucional de la Universidad de Burgos
RD 22-nov-2024