Synthesis of quaternary stereogenic centres via stereoselective intermolecular Friedel–Crafts reactions?

Organic & Biomolecular Chemistry Pub Date: 2011-04-20 DOI: 10.1039/C1OB05129F

Abstract

Highly stereoselective Friedel–Crafts reactions have been performed using a chiral anthracene template to control the selectivity of the reaction. In the case of additions to fully substituted N-acyliminium ions, competitive elimination and condensation reactions were observed. Retro-Diels–Alder reaction of one of the reaction products led to a precursor that could be used for the construction of pyroglutamic acids bearing quaternary stereogenic centres.

Graphical abstract: Synthesis of quaternary stereogenic centres via stereoselective intermolecular Friedel–Crafts reactions
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