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RESEARCH PRODUCT
Cross-Metathesis Reactions as an Efficient Tool in the Synthesis of Fluorinated Cyclic β-Amino Acids
Carlos Del PozoSantos FusteroJose Luis AcenaBegona FernandezJuan F. Sanz-cerveraMaría Sánchez-rosellóAmparo Asensiosubject
Chiral auxiliaryCyclic compoundHalogenationOrganic ChemistryAmino Acids CyclicStereoisomerismCondensation reactionChemical synthesisCatalysischemistry.chemical_compoundchemistrySalt metathesis reactionOrganic chemistryReactivity (chemistry)Chemoselectivitydescription
The synthesis of enantiomerically pure, cyclic, gamma,gamma-difluorinated beta-amino acids with various ring sizes has been carried out with a cross-metathesis (CM) reaction being one of the key steps, followed by a Dieckmann-type condensation to bring about the cyclization. Subsequent catalytic hydrogenation under microwave irradiation with (-)-8-phenylmenthol as a chiral auxiliary led to the successful chemo- and diastereoselective chemical reduction of the resulting cyclic beta-enamino esters. The efficiency and scope of the CM reaction with different types of fluorinated imidoyl chlorides and unsaturated esters has also been studied in order to determine the optimal reaction conditions with regard to selectivity and reactivity.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-04-08 | The Journal of Organic Chemistry |