Access to Highly Functionalized Sulfonated Cyclopentanes by Acid-Promoted Rauhut-Currier Reaction with Sulfinamides.

Chemistry

Université Paris-Sud, UMR CNRS 8076 BioCIS, LabEx Lermit, Equipe de Chimie des Substances Naturelles, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry (France).

Published: October 2015

An unexpected acid-mediated cascade reaction induced by conjugate addition of sulfinamides to dienediones has been developed. This highly efficient Rauhut-Currier reaction enables the rapid, high-yielding construction of sulfonated cyclopentanes with three contiguous stereogenic centers in a single operation starting from simple sulfinamides. This process constitutes the first example of sulfinamide-promoted cycloisomerization.

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Source
http://dx.doi.org/10.1002/chem.201502816DOI Listing

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