Recent Developments in Asymmetric Aziridination

Pellissier, Hélène

doi:10.1002/adsc.201400312

Cited by 127 publications

(56 citation statements)

References 213 publications

(185 reference statements)

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“…Looking at significance of asymmetry in structure of the molecules in biological systems, efforts are on to synthesize enantioenriched aziridines. 9,10 Figure 1. Main synthetic approaches to aziridines.…”

Section: Synthesis Of Aziridinesmentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

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The inherent reactivity of the aziridine ring due to ring-strain makes it valuable building blocks for the synthesis of other heterocyclic motifs of biological relevance. Of particular significance is the generation of azomethine ylides from them and cycloaddition of ylides with alkenes, alkynes, and heterocumulenes. The ring undergoes opening followed by cyclization with a variety of reagents either in the presence of a catalyst or without any catalyst. This review article discusses the recent applications of aziridines in syntheses of four-to seven-membered heterocycles of biological relevance such as azetidines, 2

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Section: Synthesis Of Aziridinesmentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

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“…Ring expansion of aziridines leading to six-membered rings through other processes than [2,3] [106] reported the total synthesis of (S)-coniine 188 from a homochiral methylene-aziridine 185. Nucleophilic ring opening is effected by a Grignard reagent in the presence of copper(I).…”

Section: Ring Expansions Of Nonactivated Aziridines and Azetidinesmentioning

confidence: 98%

“…The major one, oxazepine 226 arises from a [2,3] Meisenheimer rearrangement, which is the unique process when the oxygen atom is in a cis-relationship with the adjacent alkenyl moiety, and the minor one 227 is produced from the other trans diastereomer, through a [1,2] Meisenheimer rearrangement, giving rise to a transient isoxazoline, which is further oxidized to nitrone 227 (Scheme 60); note that 226 can be converted to the isoxazolidine by simple heating. This [2,3] Meisenheimer rearrangement served as a key step for the preparation of an analogue of (À)-debromoeudistomin K, a natural indolic alkaloid, which showed similar activity against the influenza virus compared to the natural molecule [117]. Our group recently reinvestigated this ring-expansion process of differently substituted azetidines into isoxazolidine through a [1,2] Meisenheimer rearrangement, in order to gain better knowledge of the issues of regio-and stereoselectivity of this reaction [118].…”

Section: Expansions Into Isoxazolidinesmentioning

confidence: 99%

“…Nevertheless, it rearranged quantitatively into 1,2-oxazine 224 upon attempted recrystallization in boiling DCM. This compound was produced, as suggested by the authors, either from a Cope-type elimination, followed by tautomerism of the enol into aldehyde and lactol formation, or from a direct [1,2] rearrangement (Scheme 59).…”

Section: Expansions Into Isoxazolidinesmentioning

confidence: 99%

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Ring Expansions of Nonactivated Aziridines and Azetidines

Couty

David

2015

Topics in Heterocyclic Chemistry

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Ring expansions promoted by ring strain in aziridines and azetidines are reviewed in this chapter, putting emphasis on recent applications from the last decade. This vast subject cannot be surveyed here exhaustively, and the reader will be guided to relevant precedent reviews or key reports. Rather, special attention will be put on selected examples and their mechanistic details, aiming to demonstrate that high selectivity can be reached in these reactions. In this issue, this fastgrowing topic has been divided into two distinct chapters, this one dealing with "nonactivated" aziridines and azetidines. Therefore, the reader will only find here examples involving NH-or N-alkylaziridines and N-azetidines as substrates for ring expansions, while N-acyl, N-carbamoyl, or N-tosyl compounds, defined as "activated" substrates, will be presented in the next chapter. This distinction can appear quite arbitrary at first sight but is amply justified by the great difference in reactivity of these distinct substrates. The first part focuses on the ring expansions of nonactivated aziridines into up to seven-membered rings and is further divided into expansions involving the incorporation of one (or more) heteroatoms, followed by ring expansions involving only incorporation of carbon atoms. The same model is then followed for azetidines.

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“…In view of their interesting chemical peculiarities and the scarcity of widespread procedures for their preparation [10], the scientific community is constantly interested in the development of new synthetic protocols which are more efficient than traditional methods such as cyclization of amino alcohols or the reaction between imines and diazo-containing compounds [9,11,12].…”

Section: Introductionmentioning

confidence: 99%

Aziridination of alkenes promoted by iron or ruthenium complexes

Damiano

Intrieri

Gallo

2018

Inorganica Chimica Acta

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Molecules containing an aziridine functional group are a versatile class of organic synthons due to the presence of a strained three member, which can be easily involved in ring-opening reactions and the aziridine functionality often show interesting pharmaceutical and/or biological behaviours. For these reasons, the scientific community is constantl y interested in developing efficient procedures to introduce an aziridine moiety into organic skeletons and the one-pot reaction of an alkene double bond with a nitrene [NR] source is a powerful synthetic strategy.Herein we describe the catalytic activity of iron or ruthenium complexes in promoting the reaction stated above by stressing the potential and limits of each synthetic protocol.

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Recent Developments in Asymmetric Aziridination

Cited by 127 publications

References 213 publications

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Ring Expansions of Nonactivated Aziridines and Azetidines

Aziridination of alkenes promoted by iron or ruthenium complexes

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