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Stereoselective oxa-Michael addition of tyrosine to propargyl aldehyde/esters: formation of benzofurans and flavones
Adv Synth Catal, v. 361, p. 4243-4254
Article em En | SES-SP, SESSP-IBPROD, SES-SP | ID: bud-3028
Biblioteca responsável: BR78.1
ABSTRACT
The steroselective oxa-Michael addition of the phenol moiety present in tyrosine and 3-iodotyrosine to different propargyl aldehydes delivered products with predominantly Z stereochemistry, as evidenced by X-ray crystallography analysis. When ethyl ropiolate was used as the propargyl ester source, the products were achieved with exclusively E stereochemistry with yields ranging from 17% to 91%. The oxa-Michael addition compounds served as substrates in the synthesis of 5- and 6-membered heterocyclic compounds. The atmosphere applied to the reaction medium directly influenced the formation of the products. When an inert atmosphere of nitrogen was applied, a 2-aryl-3-formyl-5-alanylbenzofuran core was selectively obtained via a Heck intramolecular reaction, while the reactions carried out under a carbon monoxide atmosphere led exclusively to 6-alanyl-2-arylflavone derivatives via reductive intramolecular acylation.
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Texto completo: 1 Coleções: 06-national / BR Base de dados: SES-SP / SESSP-IBPROD Idioma: En Revista: Adv Synth Catal Ano de publicação: 2019 Tipo de documento: Article

Texto completo: 1 Coleções: 06-national / BR Base de dados: SES-SP / SESSP-IBPROD Idioma: En Revista: Adv Synth Catal Ano de publicação: 2019 Tipo de documento: Article