Journal Article10.1039/B006015L
Aziridines: epoxides’ ugly cousins?
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TL;DR: The similarities and differences between oxiranes and their nitrogenated analogues are summarized, concentrating on the underlying properties of aziridines and recent developments in their chemistry.
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Abstract: Aziridines, the nitrogenous analogues of epoxides, have until recently excited far less interest amongst synthetic organic chemists than their oxygenated counterparts, with some justification. A range of reviews concerned with the physical properties, synthesis (asymmetric and otherwise), reactions and utility of aziridines exists; this review briefly summarizes the similarities and differences between oxiranes and their nitrogenated analogues, concentrating on the underlying properties of aziridines and recent developments in their chemistry. In addition to descriptions of the physical nature of aziridines, especially those features which underpin their utility as synthetic intermediates, the sections beneath describe reactions involving alkylative ring-opening and synthesis of aziridines.
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Citations
Enantioselective synthesis of 4,5-dihydropyrroles via domino ring-opening cyclization (DROC) of N-activated aziridines with malononitrile.
TL;DR: The DROC reaction serves as a tool for the synthesis of a large variety of substituted 4,5-dihydropyrroles in enantiomerically pure forms.
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Lewis acid-catalyzed formal [3+2] cycloadditions of N-tosyl aziridines with electron-rich alkenes via selective carbon-carbon bond cleavage.
TL;DR: A novel, mild, robust catalyst Y(OTf)(3) for C-C bond heterolysis of N-tosyl aziridines was developed and the resulting metallo-azomethine ylides may readily undergo [3+2] dipolar cycloaddition with an electron-rich olefin via a stepwise reaction pathway with high regio- and diastereoselectivity leading to substituted pyrrolidines.
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Organocatalyzed Anionic Ring-Opening Polymerizations of N-Sulfonyl Aziridines with Organic Superbases
Xin Wang,Liu Yaya,Zhenjiang Li,Haixin Wang,Hailemariam Gebru,Chen Siming,Zhu Hui,Wei Fulan,Kai Guo +8 more
TL;DR: In this paper, the anionic ring-opening polymerizations of N-sulfonyl aziridines, in the presence of organic superbases including phosphazene (t-Bu-P4), Verkade's base (P(i-PrNCH2CH2)3N, TiPP), DBU, MTBD, and N,N,N-N′,N′-tetramethylguanidine (TMG), using N-benzyl-p-toluenesulfonamide (BnN(
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Syntheses of Imidazo-, Oxa-, and Thiazepine Ring Systems via Ring-Opening of Aziridines/Cu-Catalyzed C–N/C–C Bond Formation
TL;DR: A simple and unpredicted synthetic pathway toward racemic and scalemic tetrahydrodibenzoimidazoazepines has been invented serendipitously proceeding through an S(N)2-type ring-opening of N-activated aziridines with 2-bromobenzylamine followed by a hitherto unprecedented cascade cyclization reaction sequence.
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Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza-Darzens Reactions
TL;DR: A Zn-ProPhenol catalyzed aza-Darzens reaction using chlorinated aromatic ketones as nucleophilic partners for the efficient and enantioselective construction of complex trisubstituted aziridines is reported.
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