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• W2950659256 abstract "New 1,5-dimethyl-4-phenylimidazolidin-2-one-derived acyclic chiral iminic glycine reagents have been prepared and diastereoselectively alkylated with activated alkyl halides and electrophilic olefins in the presence of lithium chloride under (a) strong bases (LHMDS, KOBu(t)) and low temperature (-78 degrees C) conditions, (b) solid-liquid phase-transfer catalysis reaction (LiOH, TBAB, -20 degrees C) conditions, and (c) in the presence of organic bases (DBU, BEMP, TMG, -20 degrees C). In the case of dielectrophiles C- and N-alkylation takes place to afford heterocyclic derivatives. Hydrolysis of alkylated products has been carried out (a) in two-step procedures with LiOOH or LiOH followed by acidic hydrolysis or Dowex purification, (b) in one single-step under refluxing water to give the corresponding alpha-amino acid, (c) in the presence of DBU in methanol to provide N-protected alpha-amino acids methyl esters, or (d) by a protection-hydrolysis procedure to afford N-Boc-protected alpha-amino acids. The chiral imidazolidinone has generally been recovered in good yield. This methodology has been shown to be useful for the synthesis of acyclic and heterocyclic (S)- and (R)-alpha-amino acids." @default.
• W2950659256 created "2019-06-27" @default.
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• W2950659256 date "2000-09-22" @default.
• W2950659256 modified "2023-10-16" @default.
• W2950659256 title "1,5-Dimethyl-4-phenylimidazolidin-2-one-Derived Iminic Glycinimides: Useful New Reagents for Practical Asymmetric Synthesis of α-Amino Acids" @default.
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• W2950659256 doi "https://doi.org/10.1021/jo000321t" @default.
• W2950659256 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/11076588" @default.
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