2026-04-23T00:00:29Zhttps://riubu.ubu.es/oai/request

oai: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 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. 2020-10-29T11:32:16Z 2020-10-29T11:32:16Z 2020-10-29T11:32:16Z 2020-10 info:eu-repo/semantics/article 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 American Chemical Society