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
- Caroli Rezende, Marcos
- Araya Maturana, Ramiro
- Maestro, M. Carmen
- García Ruano, José L.
DOIAbstract
Diels-Alder cycloaddition of 8,8-dimethylnaphthalene-1,4,5(8H)-trione with diastereomeric hydroxysulfinyldienes proceeded with high yields and good π-facial and regioselectivities. The hydroxysulfoxide moiety controls the regio- and stereoselectivities, through hydrogen bonds in the suggested transition state. © 2012 Elsevier Ltd. All rights reserved
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