Facile synthesis of asymmetric quaternary centers based on diastereoselective protection of the carbonyl group at the symmetrical position

The C2-side chain hydroxyl group of 1,3-cycloalkanedione discriminates between two ketones depending on its chirality. It chooses one ketone to form hydrogen bond with the oxygen atom of the TBDPS-oxymethyl group, but chooses the other ketone upon conversion to the isopropyl acetal. Two optically pure diastereomers, whose absolute configuration at the angular position is opposite for each other, were thus synthesized from this single chiral source through simple operations. This method may be applied for the synthesis of a variety of compounds with asymmetric quaternary centers.

Graphical abstractDownload full-size image