143086-90-2

Upstream product

• 143086-89-9 N-Isopropyl-N-methyl-2-oxo-2-phenyl-acetamide 
• 143168-25-6 [(2S,3S)-3-(Hydroxy-diphenyl-methyl)-1,4-dioxa-spiro[4.4]non-2-yl]-diphenyl-methanol; compound with N-isopropyl-N-methyl-2-oxo-2-phenyl-acetamide 

Relevant academic research and scientific papers

Designs of host/guest molecular and crystal structures

When an optically active host compound was mixed with an achiral guest compound in the solid state, host-guest inclusion crystals were formed by molecular movement and the achiral molecules became arranged in a chiral form in the inclusion crystals.

Chiral Arrangement of N-Ethyl-N-isopropylphenylglyoxylamide Molecule in Its Own Crystal and in an Inclusion Crystal with a Host Compound and Their Photoreactions in the Solid State That Give Optically Active β-Lactam Derivatives. X-ray Analytical and CD Spectral Studies

N-Ethyl-N-isopropylphenylglyoxylamide (3c) forms chiral crystal in which its achiral molecules are arranged in a chiral form, and the chirality in the crystal was identified by measurement of the CD spectrum in Nujol mull. Generation of the chirality occurs by twisting of the CO-CO bond of 3c in the crystal. Photoirradiation of the chiral crystal of 3c in the solid state gave optically active β-lactam derivative (4c) of 80% ee. By X-ray analysis, absolute configurations of the chiral crystal and 4c were elucidated. The achiral molecules of 3c are also arranged in chiral forms in inclusion complexes with chiral hosts such as (R,R)-(-)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4,4]nonane (5a), (R,R)-(-)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[5.4]-decane (5b), and their (S,S)-(+)-enantiomers, 6a and 6b, respectively. The crystal structure of a 1:1 inclusion complex of 3c with 5b (7b) was analyzed. Photoirradiation of 7b in the solid state gave (R)-(+)-4c of 85% ee. Photochemical conversions of some other derivatives of 3c to the corresponding β-lactams were also studied. Interestingly, however, irradiation of the 1:1 inclusion complex of N,N-dimethylglyoxylamide (3a) with 5a, which had been prepared by mixing both components in the absence of solvent, gave (R)-(+)-β-lactam (9a) of 45% ee, although the 1:1 complex that had been prepared by recrystallization of the components from toluene gave (S)-(-)-9a of 100% ee. Mixing of powdered chiral (-)-3c crystal with a 2:1 inclusion complex of 5b and MeOH gave a new 1:1 complex of 5b and chiral (+)-3c. The inversion of the chirality of 3c in the solid state was studied by continuous measurements of CD spectra in Nujol mulls.

Achiral molecules move and order themselves in a chiral form in host-guest inclusion crystals

When optically active host compound was mixed with achiral guest compound in the solid state, host-guest inclusion crystals were formed by molecular movement and the achiral molecules became arranged in a chiral form in the inclusion crystals.Mixing of powdered (+)-host crystals with powdered (-)-guest crystals which are formed by a chiral arrangement of achiral guest molecules gave inclusion crystals of (+)-host and the (+)-guest molecules newly produced through an inversion of the (-)-guest molecules during the complexation in the solid state.

Photocyclisation of Phenylglyoxylamides as Inclusion Complexes with an Optically Active Host Derived from Tartaric Acid: Delicate Dependence on the Substituent of the Host and Glyoxylamide

Optically active β-lactams and/or oxazolidinones have been obtained selectively by photoirradiation of a 1:2 inclusion complex of phenylglyoxylamide with an optically active host derived from tartaric acid.Delicate selectivity which is dependent on substituents in the phenylglyoxylamide and the host is described.