2026-04-23T00:04:39Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/55352021-11-02T12:05:28Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
Merging α-Lithiation and Aldol-Tishchenko Reaction to Construct Polyols from Benzyl Ethers
Sedano Labrador, Carlos
Velasco, Rocío
Suarez Pantiga, Samuel
Sanz Díez, Roberto
Reaction products
Aldehydes
Ethers
Pharmaceuticals
Aldol reactions
Química orgánica
Chemistry, Organic
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.
Ministerio de Ciencia e Innovación and FEDER (CTQ2016-75023-C2-1-P) and Junta de Castilla y León and FEDER (BU291P18)
2020-10-29T11:32:16Z
2020-10-29T11:32:16Z
2020-10
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
1523-7060
http://hdl.handle.net/10259/5535
10.1021/acs.orglett.0c03014
1523-7052
eng
Organic Letters. 2020, V. 22, n. 20, p. 8070–8075
https://doi.org/10.1021/acs.orglett.0c03014
info:eu-repo/grantAgreement/MICINN/CTQ2016-75023-C2-1-P
info:eu-repo/grantAgreement/JCyL/BU291P18
info:eu-repo/semantics/openAccess
application/pdf
American Chemical Society