Structures and Photoreactivities of N-Isopropyl-N-methylphenylglyoxylamide Included in Two Clathrate Crystals as a Guest

Abstract

Abstract The achiral N-isopropyl-N-methylphenylglyoxylamide molecule forms 1 : 2 host–guest complexes with the two kinds of the chiral host molecules derived from tartaric acid. The guest molecules in both of the clathrate crystals, I and II, are converted to the chiral β-lactam and oxazolidinone on exposure to a Hg lamp. The crystal structures of I and II, which are very similar to each other, were determined by X-rays: (I) Bis[(R,R)-(−)-trans-2,3-bis(diphenylhydroxymethyl)-1,4-dioxaspiro(4.4)nonane]N-isopropyl-N-methylphenylglyoxylamide, (C33H32O4)2·(C12H15NO2), fw = 1190.49, a = 10.404(2), b = 34.056(3), c = 9.434(3) Å, β = 94.87(2)°, V = 3331(1) Å3, Final R became 0.056. (II) Bis[(R,R)-(−)-trans-2,3-bis(diphenylhydroxymethyl)-1,4-dioxaspiro(4.5)decane]N-isopropyl-N-methylphenylglyoxylamide, (C34H34O4)2·(C12H15NO2), fw = 1218.54, a = 10.4616(5), b = 34.358(2), c = 9.469(4) Å, β = 94.798(3)°, V = 3391.4(3) Å3, Final R became 0.052. The guest molecule in each crystal is hydrogen bonded to the two host molecules. The absolute configurations of the chiral products seem to depend on the conformations of the guest molecules in I and II.