1,2,3-Trisubstituted Indanes via Tandem Conjugate Additions

Significance

The method provides a simple way to prepare highly substituted indane molecules. In one domino sequence, a boronic acid added to the unsaturated system and the resulting enolate cyclizes on the pendant second Michael acceptor. The diastereoselectivity observed was good and favored the thermodynamically more stable all-trans product. Though esters were not suitable substrates for the reaction, the authors showed that they could still be accessed via a Baeyer-Villiger oxidation of the phenyl ketones.