INQUISUR   21779
INSTITUTO DE QUIMICA DEL SUR
Unidad Ejecutora - UE
artículos
Título:
Efficient asymmetric TADDOLs-organocatalyzed cycloaddition for the synthesis of allyltin derivatives
Autor/es:
OCAMPO, ROMINA; SCOCCIA, JIMENA; COSTANTINO, ANDREA; MONITEL, MARÍA GABRIELA; GERBINO, DARÍO; ZUÑIGA, ADRIANA; PEREYRA, MARCELO T.; KOLL, LILIANA; MANDOLESI, SANDRA
Revista:
CATALYSIS COMMUNICATIONS
Editorial:
ELSEVIER SCIENCE BV
Referencias:
Lugar: Amsterdam; Año: 2014 vol. 58 p. 209 - 214
ISSN:
1566-7367
Resumen:
We report here the results obtained in the study of organocatalytic asymmetric Diels-Alder reactions to optimize the synthesis of stereo defined allyltin derivatives using (Z)-2-(1-cyclohexenyl)-1-ethenyl(trineophyl)stannane (1) as diene and substituted dienophiles in the presence of (4R,5R)-,,´,´-tetraphenyl-1,3-dioxolane-4,5-dimethanol (TADDOL, I) and analogs (4R,5R)-,,´,´-tetra(1-naphtyl)-1,3-dioxolane-4,5-dimethanol (II) and (4R,5R)-,,´,´-tetra(9-phenantryl)1,3-dioxolane-4,5-dimethanol (III) as chiral catalysts to enhance stereoselectivity through hydrogen bond activation of the dienophile. Catalyst II provides excellent results and ultrasonic radiation at low temperature showed the shorter reaction times.