Exploring the chemo-, regio-, and stereoselectivities of the (3 + 2) cycloaddition reaction of 5,5-dimethyl-3-methylene-2-pyrrolidinone with C,N-diarylnitrones and nitrile oxide derivatives: a DFT study
Sign Up to like & getrecommendations! Published in 2021 at "Journal of Molecular Modeling"
DOI: 10.1007/s00894-021-04911-0
Abstract: The (3 + 2) cycloaddition (32CA) reaction is an efficient method for the synthesis of many biologically active heterocyclic compounds, but there are several regio- and stereochemical issues that must be fully understood to exploit the full… read more here.
Keywords: nitrile oxide; usepackage; methylene pyrrolidinone; oxide derivatives ... See more keywords
The strain-promoted alkyne-nitrone and alkyne-nitrile oxide cycloaddition reactions: A theoretical study
Sign Up to like & getrecommendations! Published in 2017 at "Tetrahedron"
DOI: 10.1016/j.tet.2017.06.038
Abstract: Abstract Density functional theory (DFT) calculations were performed to study the mechanism of bioorthogonal strain-promoted dibenzocyclooctyne (DIBO)-nitrone and DIBO-nitrile oxide cycloaddition (CA) reactions at B3LYP/6-31G(d,p), M06-2X/6-31G(d,p) and B3LYP-D3/6-31G(d,p) levels of theory. The potential energy surface… read more here.
Keywords: cycloaddition reactions; nitrile oxide; study; strain promoted ... See more keywords
Nitrile oxide cycloaddition to 4-hydroxy-2-cyclopentenone: Solvent effect and selectivity
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DOI: 10.1016/j.tetlet.2017.07.056
Abstract: Abstract The facial selectivity in the nitrile oxide cycloaddition reactions of 4-hydroxy-2-cyclopentenone and its bulky t- butyloxy derivative is reported. A quantitative evaluation of the solvent effect on the hydrogen bonding directing ability is given,… read more here.
Keywords: nitrile oxide; hydroxy cyclopentenone; effect; solvent effect ... See more keywords
Total Synthesis of (+)-Pochonin D and (+)-Monocillin II via Chemo- and Regioselective Intramolecular Nitrile Oxide Cycloaddition.
Sign Up to like & getrecommendations! Published in 2017 at "Organic letters"
DOI: 10.1021/acs.orglett.7b03054
Abstract: Asymmetric total syntheses of (+)-pochonin D (1) and (+)-monocillin II (2), Hsp90 inhibitors with potent anticancer activity, have been accomplished where the macrolactone 3 was constructed through a chemo- and regioselective intramolecular nitrile oxide cycloaddition… read more here.
Keywords: regioselective intramolecular; nitrile oxide; pochonin monocillin; chemo regioselective ... See more keywords
Synthetic Study on Acremoxanthone A, Part 2: Model Study on the EFG Xanthone Moiety through a Nitrile Oxide Cycloaddition–SNAr Sequence
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DOI: 10.1055/a-1303-5613
Abstract: Toward a total synthesis of acremoxanthone A, we report a model study on the construction of the EFG ring system. The key steps include (1) an intermolecular 1,3-dipolar cycloaddition of an aryl nitrile oxide with… read more here.
Keywords: cycloaddition; model study; nitrile oxide; study ... See more keywords
Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines
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DOI: 10.3390/molecules28062547
Abstract: The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods… read more here.
Keywords: dipolar cycloaddition; syntheses isoxazolines; metathesis; nitrile oxide ... See more keywords