Enantiopure delta-hydroxy-beta-enamino ketones

The absolute configurations of 2-(alpha-methylbenzylamino)3-(1-hydroxy-1-methylethyl)cyclopent-1-en-1-yl phenyl ketone, C23H27NO2, and 5-hydroxy-4,6,6-trimethyl-3-(alpha-methylbenzylamino)-1-phenyl-2-hepten-1-one monohydrate, C24H31NO2. H2O, Obtained by a directed enantioselective aldol condensation, have been ascertained to be (alpha R, 3S) and (alpha R, 4S, 5S), respectively. While in the first cyclic delta-hydroxy-beta-enamino ketone the enaminic N atom is hydrogen bonded to the carbonyl O atom, in the second acyclic compound, the N atom is hydrogen bonded to the hydroxyl group.