The synthesis of C2 symmetry diesters of (3R,4R)-TTFOL through a green and stereoselective (2R,3R)-TADDOL rearrangement

An efficient, green, and atom economic methodology for the stereoselective synthesis of C2 symmetry (3R,4R)-TTFOL diester derivatives has been developed. The procedure occurs through a (2R,3R)-TADDOL dioxolane cleavage and rearrangement under mild conditions by its reaction with a carboxylic acid in...

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Detalles Bibliográficos
Autores: Costantino, Andrea Rosana, Montiel Schneider, María Gabriela, Galmádez, Antonio, Ocampo, Romina Andrea, Mandolesi, Sandra Delia, Koll, Liliana Cristina
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2015
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/40477
Acceso en línea:http://hdl.handle.net/11336/40477
Access Level:acceso abierto
Palabra clave:Ttfol
Green Chemistry
Atom Economy
Taddol Rearrangement
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descripción
Sumario:An efficient, green, and atom economic methodology for the stereoselective synthesis of C2 symmetry (3R,4R)-TTFOL diester derivatives has been developed. The procedure occurs through a (2R,3R)-TADDOL dioxolane cleavage and rearrangement under mild conditions by its reaction with a carboxylic acid in the presence of TFAA/H3PO4 without the need for an inert atmosphere to give generally high yields.