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Stereoselective synthesis of 1-amino-2-azidocyclopropanecarboxylic acid derivatives

(2018) LETTERS IN ORGANIC CHEMISTRY. 15(5). p.349-351
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Abstract
2-Azidocyclopropane-1,1-dicarboxylic esters were transformed into orthogonally N-protected alkyl 1-amino-2-azidocyclopropanecarboxylates via stereoselective monosaponification and subsequent Curtius reaction. Following deprotection of the ester function or the Boc-protected amino group, the first derivatives of a novel class of conformationally constrained cyclopropane alpha,beta-diamino carboxylic acids were made accessible.
Keywords
Cyclopropanes, alpha_beta-diamino carboxylic acids, azides, Curtius reaction, stereoselective synthesis, 1-aminocyclo-propanecarboxylic acid, ALPHA-AMINO-ACIDS, ALPHA, BETA-DIAMINO ACIDS, 1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACID, BIOLOGICAL SIGNIFICANCE, ETHYLENE BIOSYNTHESIS, STAUDINGER REDUCTION, PEPTIDE, RECEPTOR, DESIGN, ESTERS

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Citation

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MLA
Mangelinckx, Sven, et al. “Stereoselective Synthesis of 1-Amino-2-Azidocyclopropanecarboxylic Acid Derivatives.” LETTERS IN ORGANIC CHEMISTRY, vol. 15, no. 5, 2018, pp. 349–51, doi:10.2174/1570178614666171130162824.
APA
Mangelinckx, S., Peeters, S., & De Kimpe, N. (2018). Stereoselective synthesis of 1-amino-2-azidocyclopropanecarboxylic acid derivatives. LETTERS IN ORGANIC CHEMISTRY, 15(5), 349–351. https://doi.org/10.2174/1570178614666171130162824
Chicago author-date
Mangelinckx, Sven, Sietske Peeters, and Norbert De Kimpe. 2018. “Stereoselective Synthesis of 1-Amino-2-Azidocyclopropanecarboxylic Acid Derivatives.” LETTERS IN ORGANIC CHEMISTRY 15 (5): 349–51. https://doi.org/10.2174/1570178614666171130162824.
Chicago author-date (all authors)
Mangelinckx, Sven, Sietske Peeters, and Norbert De Kimpe. 2018. “Stereoselective Synthesis of 1-Amino-2-Azidocyclopropanecarboxylic Acid Derivatives.” LETTERS IN ORGANIC CHEMISTRY 15 (5): 349–351. doi:10.2174/1570178614666171130162824.
Vancouver
1.
Mangelinckx S, Peeters S, De Kimpe N. Stereoselective synthesis of 1-amino-2-azidocyclopropanecarboxylic acid derivatives. LETTERS IN ORGANIC CHEMISTRY. 2018;15(5):349–51.
IEEE
[1]
S. Mangelinckx, S. Peeters, and N. De Kimpe, “Stereoselective synthesis of 1-amino-2-azidocyclopropanecarboxylic acid derivatives,” LETTERS IN ORGANIC CHEMISTRY, vol. 15, no. 5, pp. 349–351, 2018.
@article{8598741,
  abstract     = {{2-Azidocyclopropane-1,1-dicarboxylic esters were transformed into orthogonally N-protected alkyl 1-amino-2-azidocyclopropanecarboxylates via stereoselective monosaponification and subsequent Curtius reaction. Following deprotection of the ester function or the Boc-protected amino group, the first derivatives of a novel class of conformationally constrained cyclopropane alpha,beta-diamino carboxylic acids were made accessible.}},
  author       = {{Mangelinckx, Sven and Peeters, Sietske and De Kimpe, Norbert}},
  issn         = {{1570-1786}},
  journal      = {{LETTERS IN ORGANIC CHEMISTRY}},
  keywords     = {{Cyclopropanes,alpha_beta-diamino carboxylic acids,azides,Curtius reaction,stereoselective synthesis,1-aminocyclo-propanecarboxylic acid,ALPHA-AMINO-ACIDS,ALPHA,BETA-DIAMINO ACIDS,1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACID,BIOLOGICAL SIGNIFICANCE,ETHYLENE BIOSYNTHESIS,STAUDINGER REDUCTION,PEPTIDE,RECEPTOR,DESIGN,ESTERS}},
  language     = {{eng}},
  number       = {{5}},
  pages        = {{349--351}},
  title        = {{Stereoselective synthesis of 1-amino-2-azidocyclopropanecarboxylic acid derivatives}},
  url          = {{http://dx.doi.org/10.2174/1570178614666171130162824}},
  volume       = {{15}},
  year         = {{2018}},
}

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