0000000000615405

AUTHOR

Laia Albert

showing 3 related works from this author

An efficient entry to optically active anti- and syn-beta-amino-alpha-trifluoromethyl alcohols.

2008

The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.

chemistry.chemical_compoundTrifluoromethylNitrogen atomStereochemistryChemistryLactolOrganic ChemistryImineDiastereomerPhysical and Theoretical ChemistryOptically activeBiochemistryOrganic letters
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Straightforward Stereoselective Access to Cyclic Peptidomimetics

2009

The preparation of cyclic dipeptide mimetics from chiral imino lactones derived from (R)-phenylglycinol is described. Key steps of the synthetic route included the fully stereoselective construction of a quaternary center, the formation of six-, seven-, or eight-membered lactams by means of an RCM cyclization, and the introduction of a new amino group within the lactam ring. The synthesis of a tripeptide mimetic is also reported.

chemistry.chemical_classificationCyclic compoundDipeptideChemistryStereochemistryMolecular MimicryOrganic ChemistryGlycineStereoisomerismDipeptidesTripeptideRing (chemistry)Peptides CyclicChemical synthesisCyclic peptideLactoneschemistry.chemical_compoundCyclizationEthanolaminesLactamLactone
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Stereoselective Access to Fluorinated and Non-fluorinated Quaternary Piperidines: Synthesis of Pipecolic Acid and Iminosugar Derivatives

2012

The preparation of optically pure quaternary piperidines, both fluorinated and non-fluorinated, has been achieved from a chiral imino lactone derived from (R)-phenylglycinol. In the case of the fluorinated derivatives, the addition of (trifluoromethyl)trimethylsilane (TMSCF(3)) followed by iodoamination and migration of the CF(3) group allowed access to four derivatives of α-(trifluoromethyl)pipecolic acid. A theoretical study of the CF(3)-group rearrangement has been carried out to help establish the reaction mechanism of this uncommon transformation. Moreover, a route to trifluoromethyl-substituted iminosugars was also developed through the diastereoselective dihydroxylation of suitable s…

HalogenationStereochemistryIminosugarAlkylationCatalysischemistry.chemical_compoundPiperidinesfluorineiminosugarsPipecolic acidchemistry.chemical_classificationamino acidsTrifluoromethylMolecular StructureChemistryOrganic ChemistryHalogenationStereoisomerismGeneral ChemistryImino SugarsDihydroxylationPipecolic Acidsdensity functional calculationsquaternary stereocentersStereoselectivityLactone
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