Organocatalysis in synthesis and reactions of epoxides and aziridines

Chawla, Ruchi; Singh, Atul K.; Yadav, Lal Dhar S.

doi:10.1039/c3ra00175j

Cited by 82 publications

(33 citation statements)

References 89 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…69 Rai and Yadav have reported the reaction of enamines 108, generated in situ from the reaction of aldehydes 104 and a pyrrolidine derivative 106, with 2-arylaziridines 105 forming pyrrolidines 107 as a single diastereomer in very good yields (Scheme 32). 70 The presence of a chiral carbon in aziridines was the main driving force in formation of a single diastereomer.…”

Section: Scheme 31mentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

View full text Add to dashboard Cite

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

show abstract

Section: Scheme 31mentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

View full text Add to dashboard Cite

show abstract

“…In methanol, we observed the incorporation of the MeO group at the benzylic position (5) in addition to the amino-oxyarylated product 4b ; these compounds were isolated in a combined yield of 78%. At this juncture, we reasoned a highly polar, hydroxylic and non-nucleophilic solvent such as 2,2,2-trifluoroethanol (CF 3 CH 2 OH, TFE) would completely avoid the incorporation of solvent into the products.…”

mentioning

confidence: 99%

Direct Stereospecific Synthesis of Unprotected N-H and N-Me Aziridines from Olefins

Jat

Paudyal

Gao

et al. 2014

Science

282

217

View full text Add to dashboard Cite

Despite the prevalence of the N-H aziridine motif in bioactive natural products and the clear advantages of this unprotected parent structure over N-protected derivatives as a synthetic building block, no practical methods have emerged for direct synthesis of this compound class from unfunctionalized olefins. Here, we present a mild, versatile method for the direct stereospecific conversion of structurally diverse mono-, di-, tri- and tetra-substituted olefins to N-H aziridines using O-(2,4-dinitrophenyl)hydroxylamine (DPH) via homogeneous rhodium catalysis with no external oxidants. This method is operationally simple (i.e., one-pot), scalable and fast at ambient temperature, furnishing N-H aziridines in good-to-excellent yields. Likewise, N-alkyl aziridines are prepared from N-alkylated DPH derivatives. Quantum-mechanical calculations suggest a plausible Rh-nitrene pathway.

show abstract

“…The epoxidation of a carbon-carbon double bond and the ring opening of resulting oxiranes with a wide range of nucleophiles is a common method to introduce various functional groups onto the skeleton of a certain organic scaffold [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Fluorination of some functionalized cycloalkenes through epoxidation and oxirane opening with Deoxofluor or XtalFluor-E

Remete¹,

Fülöp²,

Kiss³

2017

FLUOR. NOTES

View full text Add to dashboard Cite

show abstract

Organocatalysis in synthesis and reactions of epoxides and aziridines

Cited by 82 publications

References 89 publications

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Direct Stereospecific Synthesis of Unprotected N-H and N-Me Aziridines from Olefins

Fluorination of some functionalized cycloalkenes through epoxidation and oxirane opening with Deoxofluor or XtalFluor-E

Contact Info

Product

Resources

About