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

Karen Mollet (UGent) , Lena Decuyper (UGent) , Saskia Vander Meeren, Nicola Piens (UGent) , Karel De Winter (UGent) , Tom Desmet (UGent) and Matthias D'hooghe (UGent)
(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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Chicago
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.
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.
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.
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 13.9 (2015): 2716–2725. Print.
@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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