ChemInform Abstract: Ring‐Opening Addition Reactions of 1‐tert‐Butoxycarbonyl‐3,4‐epoxypiperidine with Amine Nucleophiles.
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.This chapter contains sections titled: General Nucleophilic Attack on Co-ordinated Esters and Amides Attack by Co-ordinated Nucleophile Hydrolysis of Amino Acid Esters and Amides Other Reactions of Nucleophiles and Carbonyl Compounds Conclusions
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We report an amine masking strategy for N-heterocyclic carbene (NHC)-catalysed redox amidation that couples release of the free nucleophile to catalytic turnover, and in doing so, enables direct reaction of electron-rich amines.
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Ring-opening addition reactions of 1-tert-butoxycarbonyl-3,4-epoxypiperidine leading to the formation of the corresponding regioisomeric trans-β -aminoalcohols were carried out with three different types of amine nucleophiles under different reaction conditions with a view to study the reactivity and regioselectivity.
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This chapter contains sections titled: Introduction Enantioselective Nucleophilic Addition to Meso-Epoxides Nitrogen-centered Nucleophiles Sulfur-centered Nucleophiles Oxygen-centered Nucleophiles Carbon-centered Nucleophiles Halide and Hydride Nucleophiles Kinetic Resolution of Racemic Epoxides Nitrogen-centered Nucleophiles Oxygen-centered Nucleophiles Carbon-centered Nucleophiles Enantioselective Rearrangements of Epoxides Conclusion References
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The reaction of 9-anthrylbenzyl hexachloroantimonate with the nucleophiles H2O, –OH, MeOH, –OMe, EtOH, –OEt, –OPri, and –N3 gave exclusively products with the anthracene structure by attack of a nucleophile on the central carbon. By contrast, the reaction of 9-α-chlorobenzylanthracene with the same nucleophiles yielded a mixture of anthracene derivatives and compounds with a quinoidal structure. In the reaction of N-(9-benzylidene-9,10-dihydroanthracen-10-y1)-NNN-trimethylammonium chloride with –SPh, –SC6H4NO2-p, and LiAlH4, α-substituted benzylanthracenes only were obtained.
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The 4‐membered ring in bicyclic azetidiniums, e.g. 1‐azabicyclo[2.n.0]alkanes ( n = 1–4), can be efficiently transformed to larger rings. This minireview focuses on the ring‐expansion of these azetidiniums to five‐ and eight‐membered nitrogen containing heterocycles (pyrrolidines, piperidines, azepanes and azocanes). The ring‐expansion is induced by nucleophiles which can be internal nucleophiles (leaving groups), or external nucleophiles.
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Amine-containing drugs often show poor pharmacological properties, but these disadvantages can be overcome by using a prodrug approach involving self-immolative linkers. Accordingly, we designed l-lactate linkers as ideal candidates for amine delivery. Furthermore, we designed linkers bearing two different cargos (aniline and phenol) for preferential amine cargo release within 15 min. Since the linkers carrying secondary amine cargo showed high stability at physiological pH, we used our strategy to prepare phosphate-based prodrugs of the antibiotic Ciprofloxacin. Therefore, our study will facilitate the rational design of new and more effective drug delivery systems for amine-containing drugs.
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