Carbenoid transfer to imines: a new heterogeneous catalytic synthesis of aziridines

Mohan, Jakkam Madan; Uphade, Balu S.; Choudhary, Vasant R.; Ravindranathan, T.; Sudalai, A.

doi:10.1039/a702745a

Cited by 40 publications

(1 citation statement)

References 7 publications

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“…This mode is extensively explored for the preparation of cyclopropanes3a and epoxides 3b from olefins. Catalytic addition of a carbene moiety to imine results in the formation of aziridine, but the yields are often on lower side . Similarly, the transfer of a nitrogen atom onto an olefin offers an attractive synthesis of aziridine.…”

Section: Introductionmentioning

confidence: 99%

Investigations in the Transition Metal Catalyzed Aziridination of Olefins, Amination, and Other Insertion Reactions with Bromamine-T as the Source of Nitrene

2000

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Investigations into the transition metal catalyzed aziridination of olefins with Bromamine-T as a new source of nitrene is presented in this account. Comparison of Chloramine-T and Bromamine-T in this reaction indicates that the latter is superior as the source of nitrene. Systematic study with several transition metal based catalysts suggests that Cu-halides are the best catalysts. A first report of aziridination under microwave and ultrasound irradiation conditions is also presented. Copper-catalyzed aziridination of methyl cinnamate with Bromamine-T did not proceed at ambient temperature but was effected smoothly under ultrasound irradiation to furnish trans-aziridine selectively, while under microwave irradiation, a mixture of cis and trans isomers, was obtained. It has been demonstrated that aziridination of olefins proceeds smoothly with inexpensive bleaching powder. Preliminary results of Rh-catalyzed benzylic insertion reactions with Bromamine-T are included in this account.

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Section: Introductionmentioning

confidence: 99%

Investigations in the Transition Metal Catalyzed Aziridination of Olefins, Amination, and Other Insertion Reactions with Bromamine-T as the Source of Nitrene

2000

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Methyl Diazoacetate

Droste¹,

Audia²,

Rasappan³

et al. 2006

Encyclopedia of Reagents for Organic Synthesis

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Transition Metal Aziridination Catalysts

Chandrachud

Jenkins

2017

Encyclopedia of Inorganic and Bioinorganic Chemistry

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Aziridines are three‐membered rings containing one nitrogen and two carbon atoms. This functional group is present in many bioactive molecules in addition to being a useful synthetic intermediate that is analogous to epoxides. Since they are a strained ring system, aziridines are reactive toward nucleophilic ring opening, ring expansion, and ring rearrangement reactions. Due to their importance in synthetic chemistry, numerous approaches to their synthesis have been developed. In addition to traditional organic reaction approaches to aziridination, transition metal catalyzed versions of this reaction have been developed. The primary rationales for catalyzed aziridination includes broadening the substrate scope, increasing yields (particularly under mild conditions), and improving enantiomeric purity. These catalytic reactions can mostly be designated as one of three classes. In this article, each of these important transition metal catalyzed aziridination reaction paths will be reviewed in addition to the catalysts that perform them.

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Carbenoid transfer to imines: a new heterogeneous catalytic synthesis of aziridines

Abstract: A heterogeneous catalytic method for the preparation of trans-aziridines from imines and methyl diazoacetate is described using Rh III -and Mn III -exchanged montmorillonite K10 clays as catalysts.

Cited by 40 publications

References 7 publications

Investigations in the Transition Metal Catalyzed Aziridination of Olefins, Amination, and Other Insertion Reactions with Bromamine-T as the Source of Nitrene

Investigations in the Transition Metal Catalyzed Aziridination of Olefins, Amination, and Other Insertion Reactions with Bromamine-T as the Source of Nitrene

Methyl Diazoacetate

Transition Metal Aziridination Catalysts

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