Remote Regio- and Stereocontrol by the Sulfinyl Group: Diels-Alder Reaction of Sulfinyl Dienols and 8,8-Dimethylnaphthalene-1,4,5(8h)-Trione

Caroli-Rezende, M; Almodovar-Fajardo, I

doi:10.1016/j.tetasy.2012.11.017

Remote Regio- and Stereocontrol by the Sulfinyl Group: Diels-Alder Reaction of Sulfinyl Dienols and 8,8-Dimethylnaphthalene-1,4,5(8h)-Trione

Journal

Tetrahedron Asymmetry

ISSN

1362-511X

Date Issued

2013

Author(s)

Caroli-Rezende, M

Almodovar-Fajardo, I

DOI

https://doi.org/10.1016/j.tetasy.2012.11.017

Abstract

Diels-Alder cycloaddition of 8,8-dimethylnaphthalene-1,4,5(8H)-trione with diastereomeric hydroxysulfinyldienes proceeded with high yields and good ?-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.