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Selective elaboration of aminodiols towards small ring α- and β-amino acid derivatives that incorporate an aziridine, azetidine, or epoxide scaffold

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Abstract
The osmium-catalyzed dihydroxylation of N-substituted alkyl 2-(aminomethyl) acrylates resulted in the efficient synthesis of 2-(aminomethyl)-2,3-dihydroxypropanoates in good yields (82-89 %). The resulting aminodiols were elaborated in a selective diversity-oriented synthesis to produce the corresponding 2-(aminomethyl) oxirane-2-carboxylates, functionalized aziridine-2-carboxylates, and azetidine-3-carboxylates by using straightforward reactions.
Keywords
STEREOSELECTIVE-SYNTHESIS, STEREOSPECIFIC ANIONIC-POLYMERIZATION, Small ring systems, Dihydroxylation, Synthetic methods, Amino acids, Heterocycles, RECEPTOR ANTAGONIST, SECONDARY STRUCTURE, ALKYL 2-(BROMOMETHYL)AZIRIDINE-2-CARBOXYLATES, 3-ACYLAMINO-2-METHYLENE ALKANOATES, ASYMMETRIC DIHYDROXYLATION, AMINOHALOGENATION REACTION, BUILDING-BLOCKS, CINNAMIC ESTERS

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Citation

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MLA
Semina, Elena et al. “Selective Elaboration of Aminodiols Towards Small Ring Α- and Β-amino Acid Derivatives That Incorporate an Aziridine, Azetidine, or Epoxide Scaffold.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 9 (2016): 1720–1731. Print.
APA
Semina, E., Žukauskaitė, A., Šačkus, A., De Kimpe, N., & Mangelinckx, S. (2016). Selective elaboration of aminodiols towards small ring α- and β-amino acid derivatives that incorporate an aziridine, azetidine, or epoxide scaffold. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (9), 1720–1731.
Chicago author-date
Semina, Elena, Asta Žukauskaitė, Algirdas Šačkus, Norbert De Kimpe, and Sven Mangelinckx. 2016. “Selective Elaboration of Aminodiols Towards Small Ring Α- and Β-amino Acid Derivatives That Incorporate an Aziridine, Azetidine, or Epoxide Scaffold.” European Journal of Organic Chemistry (9): 1720–1731.
Chicago author-date (all authors)
Semina, Elena, Asta Žukauskaitė, Algirdas Šačkus, Norbert De Kimpe, and Sven Mangelinckx. 2016. “Selective Elaboration of Aminodiols Towards Small Ring Α- and Β-amino Acid Derivatives That Incorporate an Aziridine, Azetidine, or Epoxide Scaffold.” European Journal of Organic Chemistry (9): 1720–1731.
Vancouver
1.
Semina E, Žukauskaitė A, Šačkus A, De Kimpe N, Mangelinckx S. Selective elaboration of aminodiols towards small ring α- and β-amino acid derivatives that incorporate an aziridine, azetidine, or epoxide scaffold. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2016;(9):1720–31.
IEEE
[1]
E. Semina, A. Žukauskaitė, A. Šačkus, N. De Kimpe, and S. Mangelinckx, “Selective elaboration of aminodiols towards small ring α- and β-amino acid derivatives that incorporate an aziridine, azetidine, or epoxide scaffold,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no. 9, pp. 1720–1731, 2016.
@article{7256965,
  abstract     = {The osmium-catalyzed dihydroxylation of N-substituted alkyl 2-(aminomethyl) acrylates resulted in the efficient synthesis of 2-(aminomethyl)-2,3-dihydroxypropanoates in good yields (82-89 %). The resulting aminodiols were elaborated in a selective diversity-oriented synthesis to produce the corresponding 2-(aminomethyl) oxirane-2-carboxylates, functionalized aziridine-2-carboxylates, and azetidine-3-carboxylates by using straightforward reactions.},
  author       = {Semina, Elena and Žukauskaitė, Asta and Šačkus, Algirdas and De Kimpe, Norbert and Mangelinckx, Sven},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {STEREOSELECTIVE-SYNTHESIS,STEREOSPECIFIC ANIONIC-POLYMERIZATION,Small ring systems,Dihydroxylation,Synthetic methods,Amino acids,Heterocycles,RECEPTOR ANTAGONIST,SECONDARY STRUCTURE,ALKYL 2-(BROMOMETHYL)AZIRIDINE-2-CARBOXYLATES,3-ACYLAMINO-2-METHYLENE ALKANOATES,ASYMMETRIC DIHYDROXYLATION,AMINOHALOGENATION REACTION,BUILDING-BLOCKS,CINNAMIC ESTERS},
  language     = {eng},
  number       = {9},
  pages        = {1720--1731},
  title        = {Selective elaboration of aminodiols towards small ring α- and β-amino acid derivatives that incorporate an aziridine, azetidine, or epoxide scaffold},
  url          = {http://dx.doi.org/10.1002/ejoc.201600036},
  year         = {2016},
}

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