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RESEARCH PRODUCT
Differential reactivity of fluorinated homopropargylic amino esters vs gold(I) salts. The role of the nitrogen protecting group
Santos FusteroJavier MiróCarlos Del PozoMaría Sánchez-rosellósubject
chemistry.chemical_classificationCarbamateFluorinated alfa-amino acid derivativesAmino estersmedicine.medical_treatmentOrganic ChemistryFluorinated dihydro-quinolineschemistry.chemical_elementOxazinesGold catalysisTriple bondBiochemistryMedicinal chemistryNitrogenInorganic Chemistrychemistry.chemical_compoundchemistrymedicineBenzyl groupEnvironmental ChemistryFluorinated homopropargyl amino estersPhysical and Theoretical ChemistryProtecting groupFluorinated oxazinesdescription
The reaction of several homopropargyl amino esters 4, bearing aromatic substituents and a benzyl group as nitrogen substituents, with gold(I) salts gave rise to fluorinated quinolines 6 in a tandem hydroarylation-isomerization process. On the other hand, homopropargyl amino esters 7 containing a carbamate group underwent the carbonyl addition over the triple bond in the presence of gold(I) salts, rendering fluorinated oxazines 8. The use of chiral sulfoxides allowed us to develop the asymmetric version of this protocol. This two processes complete the differential reactivity showed by these types of susbtrates, depending on the nature of the nitrogen protecting group. (C) 2014 Elsevier B.V. All rights reserved.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-03-01 |