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RESEARCH PRODUCT
Catalytic Enantioselective Aza-Reformatsky Reaction with Cyclic Imines
M. Carmen MuñozCarlos VilaLode De MunckJosé R. Pedrosubject
AldimineEthyl iodoacetateBeta-amino ester010402 general chemistry01 natural sciencesCatalysisReaccions químiquesStereocenterchemistry.chemical_compoundCatàlisiAsymmetric catalysisOrganic chemistryheterocyclic compoundsReformatsky reactionchemistry.chemical_classification010405 organic chemistryOrganic ChemistryChiral ligandEnantioselective synthesisGeneral Chemistry0104 chemical sciencesProlinolCyclic ketiminesZincchemistryReformatsky reactionFISICA APLICADAReagentQuímica orgànicadescription
A catalytic highly enantioselective aza-Reformatsky reaction with cyclic aldimines and ketimines for the synthesis of chiral b-amino esters with good yields and excellent enantioselectivities is reported.Areadily available diaryl prolinol is used as a chiral ligand, ZnMe2 as a zinc source and ethyl iodoacetate as reagent in the presence of air atmosphere. The reaction with cyclic ketimines generates a quaternary stereocenter with excellent levels of enantioselectivity. Furthermore, five-membered N-sulfonyl ketimines were used as electrophiles with good enantiomeric excesses, under the optimized reaction conditions. Moreover, several chemical transformations were performed with the chiral b-amino esters.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-01-01 | Chemistry - A European Journal |