Enantioselective Cyclopropanation of 2‐Cyano‐3‐arylacrylates Using Carbohydrate‐Based Crown Ethers
Abstract: Enantioenriched, highly functionalized cyclopropane derivatives were prepared by a simple and green approach using monosaccharide‐based chiral crown ethers as phase transfer catalysts. The Michael‐initiated ring closure (MIRC) reactions of diethyl bromomalonate with 2‐cyano‐3‐phenylacrylate took place with complete diastereoselectivity in the presence of chiral lariat ethers derived from carbohydrates and enantioselectivity up to 87 % ee was achieved. Among the catalysts tested, the monoaza‐15‐crown‐5 lariat ether having a methyl β‐d‐glucopyranoside unit and a 2‐(3,4‐dimethoxyphenyl) ethyl group on the nitrogen generated the highest asymmetric induction (87 % ee). In the reactions of analogous 2‐cyano‐3‐arylacrylates, enantioselectivity was in the range of 8–91 % ee.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Enantioselective Cyclopropanation of 2‐Cyano‐3‐arylacrylates Using Carbohydrate‐Based Crown Ethers ; volume:2022 ; number:14 ; year:2022 ; extent:10
European journal of organic chemistry ; 2022, Heft 14 (2022) (gesamt 10)
- Creator
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Orbán, István
Varga, Bertalan
Bagi, Péter
Holczbauer, Tamás
Rapi, Zsolt
- DOI
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10.1002/ejoc.202200112
- URN
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urn:nbn:de:101:1-2022040715192041699956
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:37 AM CEST
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Associated
- Orbán, István
- Varga, Bertalan
- Bagi, Péter
- Holczbauer, Tamás
- Rapi, Zsolt
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The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts
Enantioselective Synthesis of 2-Carboxy Cyclic Ethers
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Enantioselective Complexation of Protonated Tyrosine by a Chiral Crown‐ether: The Nature of the Hydrogen Bonds Makes the Difference
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Tying a knot between crown ethers and porphyrins
Unveiling the nature of supramolecular crown ether–C60 interactions
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