Artículo
Efficient asymmetric TADDOLs-organocatalyzed cycloaddition for the synthesis of allyltin derivatives
Ocampo, Romina Andrea
; Scoccia, Jimena
; Costantino, Andrea Rosana
; Montiel Schneider, María Gabriela
; Gerbino, Darío César
; Zuñiga, Adriana Elena; Pereyra, Marcelo Tomas
; Koll, Liliana Cristina
; Mandolesi, Sandra Delia
Fecha de publicación:
09/2014
Editorial:
Elsevier Science
Revista:
Catalysis Communications
ISSN:
1566-7367
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
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)-α,α,α′,α′-tetraphenyl-1,3-dioxolane-4,5-dimethanol (TADDOL, I) and analogs (4R,5R)-α,α,α′,α′-tetra(1-naphtyl)-1,3-dioxolane-4,5-dimethanol (II) and (4R,5R)-α,α,α′,α′-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 provided excellent results and ultrasonic radiation at low temperature showed the shorter reaction times.
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Articulos(INQUISUR)
Articulos de INST.DE QUIMICA DEL SUR
Articulos de INST.DE QUIMICA DEL SUR
Citación
Ocampo, Romina Andrea; Scoccia, Jimena; Costantino, Andrea Rosana; Montiel Schneider, María Gabriela; Gerbino, Darío César; et al.; Efficient asymmetric TADDOLs-organocatalyzed cycloaddition for the synthesis of allyltin derivatives; Elsevier Science; Catalysis Communications; 58; 9-2014; 209-214
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