“Alternative method for the resolution of 1-benzoyl-2-tert-butyl-3-methyl-1,3-imidazolidin-4-one”

Juaristi, Eusebio; Rizo, Benito; Natal, Vicente; Escalante, Jaime; Regla, Ignacio

doi:10.1016/s0957-4166(00)80465-6

Cited by 14 publications

(7 citation statements)

References 14 publications

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“…Our result is in agreement with the configuration determined for similar compounds using chemical correlation and X-ray diffraction. 6,7 The ring conformation shown in Figure 3 resembles the envelope conformer that professor Seebach and coworkers 9 found for 2-tert-butyl-1,3-imidazolidin-4-ones with a methyl group attached to N-3. Using the CS Chem3D Pro program and the above-mentioned conformer, we modeled the structures of imidazolidinones 3-6.…”

Section: S78mentioning

confidence: 80%

“…6,7 The 1 H NMR spectra of imidazolidinones 3 and 4 obtained in deuterated chloroform at 27°C consist of one set of sharp signals, but the spectra of 5 and 6 contain broad signals. The broadening in the spectra of the latter imidazolidinones diminish either at elevated temperature or in methanol-d 4 ; therefore, for the present discussion we have taken the parameters obtained in deuterated chloroform at 60°C.…”

Section: Resultsmentioning

confidence: 99%

“…6,7 In order to investigate the possible application of the spectroscopic method for configurational analysis of the latter compounds, we have prepared the imidazolidinones 1-6 shown in Figure 1 and have studied them by 1 H and 13 C NMR and X-ray diffraction. The corresponding results are discussed in the present contribution.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and NMR configurational analysis of 1,3-imidazolidin-4-ones derived from (?)-(S)-phenylethylamine

2003

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The preparation and NMR study in the solution state of (-)-(S)-1-acetyl-3-(phenylethyl)-1,3-imidazolidin-4-one, (-)-(2R,1'S)- and (+)-(2S,1'S)-1-acetyl-2-tert-butyl-3-(phenylethyl)-1,3-imidazolidin-4-one, and (-)-(2S,1'S)- and (+)-(2R,1'S)-1-carboethoxy-2-tert-butyl-3-(phenylethyl)-1,3-imidazolidin-4-one are described. The orientations of acetyl, carboethoxy, and phenethyl groups attached to nitrogen atoms N-1 and N-2 were deduced from the proton and (13)C chemical shifts. The typical orientation of phenethyl group, which has the hydrogen H-6 syn and close to the oxygen of carbonyl C-4, was observed in (-)-(S)-1-acetyl-3-(phenylethyl)-1,3-imidazolidin-4-one but not in the other four compounds; nevertheless, interpretation of chemical shifts based on the ring current effects correlated with the true configuration of the new stereogenic center at C-2. Four of these imidazolidinones were analyzed by X-ray diffraction to corroborate the configuration determined by NMR. The structures determined by X-ray diffraction revealed the existence of intramolecular hydrogen bonds capable to control the conformation of the phenethyl and acyl groups in the solution state.

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Section: S78mentioning

confidence: 80%

Section: Resultsmentioning

confidence: 99%

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Synthesis and NMR configurational analysis of 1,3-imidazolidin-4-ones derived from (?)-(S)-phenylethylamine

2003

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“…18 Other Synthetic Building Blocks from Boc-BMI. Deoxygenation of Boc-BMI leads to the imidazolidine (16) which can be lithiated on the methylene group next to N(1), and thus converted to compounds (17); from the corresponding ester (R E = CO 2 Me), 2,3-diaminopropionic acid derivatives (18) and (19) …”

Section: Alternate Names: N-t-butoxycarbonyl-2-t-butyl-3-methylimid-mentioning

confidence: 99%

“…InChI = 1/C13H24N2O3/c1-12(2,3)10-14 (7)9(16)8-15(10)11 (17)18-13(4,5)6/h10H,8H2,1-7H3/t10-/m0/s1 InChIKey = HJJLVATZPPJBNG-JTQLQIEIBB (chiral glycine derivatives 1 for the synthesis of amino acids)…”

mentioning

confidence: 99%