Remote regio- and stereocontrol by the sulfinyl group: Diels–Alder reaction of sulfinyl dienols and 8,8-dimethylnaphthalene-1,4,5(8H)-trione

Almodovar, Iriux; Cardona, Wilson; Delgado Castro, Tomás; Zapata Torres, Gerald Amilcar; Caroli Rezende, Marcos; Araya Maturana, Ramiro; Maestro, M. Carmen; García Ruano, José L.

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2013

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Remote regio- and stereocontrol by the sulfinyl group: Diels–Alder reaction of sulfinyl dienols and 8,8-dimethylnaphthalene-1,4,5(8H)-trioneFormato de cita

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Almodovar, Iriux;
Cardona, Wilson;
Delgado Castro, Tomás;
Zapata Torres, Gerald Amilcar;
Caroli Rezende, Marcos;
Araya Maturana, Ramiro;
Maestro, M. Carmen;
García Ruano, José L.;

Abstract

Diels–Alder cycloaddition of 8,8-dimethylnaphthalene-1,4,5(8H)-trione with diastereomeric hydroxysulfinyldienes proceeded with high yields and good p-facial and regioselectivities. The hydroxysulfoxide moiety controls the regio- and stereoselectivities, through hydrogen bonds in the suggested transition state.

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URI: https://repositorio.uchile.cl/handle/2250/121855
DOI: doi10.1016/j.tetasy.2012.11.017

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Tetrahedron: Asymmetry 24 (2013) 56–61

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