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Synthesis of 2-aryl-3-(2-cyanoethyl)aziridines and their chemical and enzymatic hydrolysis towards γ-lactams and γ-lactones

(2015) ORGANIC & BIOMOLECULAR CHEMISTRY. 13(9). p.2716-2725
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Abstract
Trans- and cis-2-aryl-3-(2-cyanoethyl)aziridines, prepared via alkylation of the corresponding 2-aryl-3-(tosyloxymethyl)aziridines with the sodium salt of trimethylsilylacetonitrile, were transformed into variable mixtures of 4-aryl(alkylamino)methylIbutyrolactones and 5-[aryl(hydroxy)methyl]pyrrolidin-2-ones via KOH-mediated hydrolysis of the cyano group, followed by ring expansion. In addition, next to this chemical approach, enzymatic hydrolysis of the former aziridinyl nitrites by means of a nitrilase was performed as well, interestingly providing a selective route towards the above-mentioned functionalized gamma-lactams
Keywords
SYNTHON METHOD, BUILDING-BLOCKS, ORGANIC-SYNTHESIS, TRANSFORMATION, REACTIVITY, ASYMMETRIC-SYNTHESIS, BIOCATALYSIS, NITRILE, ENZYMES, BETA-AMINO ACIDS

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MLA
Mollet, Karen, et al. “Synthesis of 2-Aryl-3-(2-Cyanoethyl)Aziridines and Their Chemical and Enzymatic Hydrolysis towards γ-Lactams and γ-Lactones.” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 13, no. 9, 2015, pp. 2716–25, doi:10.1039/c4ob02615b.
APA
Mollet, K., Decuyper, L., Vander Meeren, S., Piens, N., De Winter, K., Desmet, T., & D’hooghe, M. (2015). Synthesis of 2-aryl-3-(2-cyanoethyl)aziridines and their chemical and enzymatic hydrolysis towards γ-lactams and γ-lactones. ORGANIC & BIOMOLECULAR CHEMISTRY, 13(9), 2716–2725. https://doi.org/10.1039/c4ob02615b
Chicago author-date
Mollet, Karen, Lena Decuyper, Saskia Vander Meeren, Nicola Piens, Karel De Winter, Tom Desmet, and Matthias D’hooghe. 2015. “Synthesis of 2-Aryl-3-(2-Cyanoethyl)Aziridines and Their Chemical and Enzymatic Hydrolysis towards γ-Lactams and γ-Lactones.” ORGANIC & BIOMOLECULAR CHEMISTRY 13 (9): 2716–25. https://doi.org/10.1039/c4ob02615b.
Chicago author-date (all authors)
Mollet, Karen, Lena Decuyper, Saskia Vander Meeren, Nicola Piens, Karel De Winter, Tom Desmet, and Matthias D’hooghe. 2015. “Synthesis of 2-Aryl-3-(2-Cyanoethyl)Aziridines and Their Chemical and Enzymatic Hydrolysis towards γ-Lactams and γ-Lactones.” ORGANIC & BIOMOLECULAR CHEMISTRY 13 (9): 2716–2725. doi:10.1039/c4ob02615b.
Vancouver
1.
Mollet K, Decuyper L, Vander Meeren S, Piens N, De Winter K, Desmet T, et al. Synthesis of 2-aryl-3-(2-cyanoethyl)aziridines and their chemical and enzymatic hydrolysis towards γ-lactams and γ-lactones. ORGANIC & BIOMOLECULAR CHEMISTRY. 2015;13(9):2716–25.
IEEE
[1]
K. Mollet et al., “Synthesis of 2-aryl-3-(2-cyanoethyl)aziridines and their chemical and enzymatic hydrolysis towards γ-lactams and γ-lactones,” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 13, no. 9, pp. 2716–2725, 2015.
@article{5946378,
  abstract     = {{Trans- and cis-2-aryl-3-(2-cyanoethyl)aziridines, prepared via alkylation of the corresponding 2-aryl-3-(tosyloxymethyl)aziridines with the sodium salt of trimethylsilylacetonitrile, were transformed into variable mixtures of 4-aryl(alkylamino)methylIbutyrolactones and 5-[aryl(hydroxy)methyl]pyrrolidin-2-ones via KOH-mediated hydrolysis of the cyano group, followed by ring expansion. In addition, next to this chemical approach, enzymatic hydrolysis of the former aziridinyl nitrites by means of a nitrilase was performed as well, interestingly providing a selective route towards the above-mentioned functionalized gamma-lactams}},
  author       = {{Mollet, Karen and Decuyper, Lena and Vander Meeren, Saskia and Piens, Nicola and De Winter, Karel and Desmet, Tom and D'hooghe, Matthias}},
  issn         = {{1477-0520}},
  journal      = {{ORGANIC & BIOMOLECULAR CHEMISTRY}},
  keywords     = {{SYNTHON METHOD,BUILDING-BLOCKS,ORGANIC-SYNTHESIS,TRANSFORMATION,REACTIVITY,ASYMMETRIC-SYNTHESIS,BIOCATALYSIS,NITRILE,ENZYMES,BETA-AMINO ACIDS}},
  language     = {{eng}},
  number       = {{9}},
  pages        = {{2716--2725}},
  title        = {{Synthesis of 2-aryl-3-(2-cyanoethyl)aziridines and their chemical and enzymatic hydrolysis towards γ-lactams and γ-lactones}},
  url          = {{http://dx.doi.org/10.1039/c4ob02615b}},
  volume       = {{13}},
  year         = {{2015}},
}

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