Pseudo enantiomeric mixed s/p ligands derived from carbohydrates for the 1,4-addition of phenyl boronic acid to cyclohexenone

Autor:	Noureddine Khiar, Alvaro Salvador, Juan Francisco Moya, Christian Rosales-Barrios, Victoria Valdivia, Nerea Bilbao, Inmaculada Fernández, Rocío Recio
Přispěvatelé:	Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica
Rok vydání:	2016
Předmět:	010405 organic chemistry Chemistry Stereochemistry General Chemical Engineering Heteroatom General Chemistry 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Cyclohexenone Reactivity (chemistry) Phenylboronic acid Enantiomer Boronic acid
Zdroj:	idUS. Depósito de Investigación de la Universidad de Sevilla instname Digital.CSIC. Repositorio Institucional del CSIC
Popis:	The application of phosphinite-thioglycosides and phosphine-thioglycosides ligands in the Rh(I)-catalyzed 1,4-addition of phenylboronic acid to cyclohexenone is reported. Among the ligands tested, phosphinite-thioglycoside 3 and phosphine-thioglycoside 10, bearing a 1,2-cis arrangement of the two heteroatoms, have exhibited the best results in terms of reactivity and enantioselectivity. Interestingly, ligands 3 and 10, both derived from D-sugar are able to generate the addition product of the phenylboronic acid to the cyclohexenone with opposite configuration, behaving thus as enantiomers
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4d0740fdb7c8485c833e632b444072c0 https://idus.us.es/handle/11441/59961 Zobrazit plný text záznamu