Search results for "Propargylic amines"

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Catalytic Enantioselective Cyclopropylalkynylation of Aldimines Generated In Situ from α-Amido Sulfones

2022

A convenient procedure of synthesis of N-carbamoyl-protected propargylic amines substituted with a cyclopropyl group from α-amido sulfones and cyclopropylacetylene is described. The reaction is catalyzed by a chiral BINOL-type zinc complex and provides the corresponding products in good yields and enantioselectivities.

Organic ChemistryPharmaceutical ScienceStereoisomerismCatalysisAnalytical ChemistryZinc<i>N</i>-carbamoyl-protected propargylic amines; α-amido sulfones; cyclopropylacetylene; BINOL; zinc complexCatàlisiChemistry (miscellaneous)Drug DiscoveryMolecular MedicineSulfonesAminesPhysical and Theoretical ChemistryQuímica orgànica
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Synthesis of Densely Functionalised 5-Halogen-1,3-oxazin-2-ones byHalogen-Mediated Regioselective Cyclisation of N-Cbz-ProtectedPropargylic Amines: A…

2013

A very efficient synthesis of 5-halogen-1,3-oxazin-2-ones has been accomplished by the halocyclisation reaction of chiral nonracemic N-carbobenzyloxy (N-Cbz)-protected propargylic amines by using I-2, Br-2 and Cl-2 as electrophile sources. The nature of the halogen influences the reaction time and yield. However, in all cases the reaction is totally regioselective taking place through a 6-endo-dig process regardless of the nature of the halogen and of the substituents in the starting material. To rationalise the experimental results, theoretical studies at the B3LYP/6-311G* level have been performed.

Propargylic aminesReaction mechanismChemistryReaction mechanismsOrganic ChemistryRegioselectivityGeneral ChemistryCatalysisOxazinonesDensity functional calculationsRegioselectivityHalocyclisationYield (chemistry)FISICA APLICADAHalogenElectrophileOrganic chemistry
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