Enantiopure δ-Hydroxy-β-enamino Ketones

The absolute configurations of 2-(α-methylbenzylamino)-3-(1′-hydroxy- 1′-methylethyl)­cyclopent-1-en-1-yl phenyl ketone, C₂₃H₂₇NO₂ and 5-hydroxy-4,6,6-trimethyl-2-hepten-1-one, C₂₄H₃₁NO₂, obtained by a directed enantioselective aldol condensation, have been ascertained to be (αR,3S) and (αR,4S,5S), respectively. While in the first cyclic δ-hydroxy-β-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.

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