Binaphthyl-based chiral bifunctional organocatalysts for water mediated asymmetric List–Lerner–Barbas aldol reactions

Autor:	Chinnadurai Chithiraikumar, Veeramanoharan Ashokkumar, Ayyanar Siva
Rok vydání:	2016
Předmět:	010405 organic chemistry Chemistry Organic Chemistry Substrate (chemistry) 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis Solvent chemistry.chemical_compound Aldol reaction Organic chemistry Physical and Theoretical Chemistry Bifunctional
Zdroj:	Organic & Biomolecular Chemistry. 14:9021-9032
ISSN:	1477-0539 1477-0520
DOI:	10.1039/c6ob01558a
Popis:	Novel binaphthyl-based chiral bifunctional organocatalysts were designed, synthesized and successfully applied to the asymmetric List-Lerner-Barbas aldol reaction in the presence of water. These organocatalysts were found to be effective catalysts for the reactions of symmetrical, unsymmetrical and cyclic ketones with different aldehydes to give the corresponding aldol products with higher yields (up to 98%) and very good ee's up to 99%. The catalytic system leads to higher yields and selectivities than the previously reported well-known proline based organocatalysts. In addition to the effect of solvent, additives, catalyst concentration, temperature and the substrate scope of the reactions were also investigated.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::392354ab4d4f90734f588763ac9ca89b https://doi.org/10.1039/c6ob01558a Zobrazit plný text záznamu