In this work, we have developed a method for the enantioselective synthesis of atropisomeric aromatic amides by the amine-catalyzed arene-forming aldol condensation. By using glyoxylic amide substrates, we have observed a particularly efficient construction of a new aromatic ring, which was complete within minutes at ambient temperature and gave products with excellent stereoselectivity. After a reduction, products with high rotational barriers were isolated and we expect these to become important spatially organized chiral scaffolds.
A strategy for the efficient synthesis of individual stereoisomers of 1,2-naphthylene oligomers is described in this publication. Iterative building block additions and consecutive stereoselective arene-forming aldol condensation reactions with catalyst-controlled atropoenantioselectivity and substrate-controlled atropodiastereoselectivity provided structurally distinct ter- and quaternaphthalene stereoisomers. These structurally highly defined oligomers represent configurationally stable analogues of otherwise stereodynamic, helically shaped ortho-phenylenes.
This work outlines our interest in alternatives to cross-coupling reactions. Carboxylic acid esters were converted in substituted arenes in one step by using 1,5-bifunctional organomagnesium reagents. Various carboxylic acid esters could be converted to prepare benzene, anthracene, tetracene, and pentacene derivatives. The reaction proceeds via a double nucleophilic addition of the 1,5-organodimagnesium reagent to the ester followed by an 1,4-elimination for an overall [5+1] construction of a new aromatic ring.
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