Synthesis of organotin derivatives of optically active eleven-membered macrodiolides

The synthesis and the results obtained in the hydrostannation of eight new TADDOL diacrylates and methacrylates are reported. The addition of triorganotin hydrides, R3SnH, 12-14 (R = nBu, neophyl, Ph, respectively) to diesters 6-11 containing different combinations of substituents at the C-2 carbon...

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Detalles Bibliográficos
Autores: Scoccia, Jimena, Gerbino, Darío César, Podestá, Julio Cesar
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2016
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/53818
Acceso en línea:http://hdl.handle.net/11336/53818
Access Level:acceso abierto
Palabra clave:Taddols Like Unsaturated Diesters Stereoselective Cyclohydrostannation
Cyclohydrostannation
Eleven Membered Macrolides
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descripción
Sumario:The synthesis and the results obtained in the hydrostannation of eight new TADDOL diacrylates and methacrylates are reported. The addition of triorganotin hydrides, R3SnH, 12-14 (R = nBu, neophyl, Ph, respectively) to diesters 6-11 containing different combinations of substituents at the C-2 carbon of the dioxolane ring, led to macrocyclization products in all cases. The cyclohydrostannation of diacrylate 10 proceeded with complete diastereoselectivity. The cyclohydrostannation of diesters 33 and 34 with hydrides 12 and 14 in all cases only afforded one stannylated macrocycle.