6533b86ffe1ef96bd12cdd88
RESEARCH PRODUCT
Diastereodivergent Synthesis of Fluorinated Cyclic β(3)-Amino Acid Derivatives.
Marta GuerolaSantos FusteroAntonio Simón-fuentesCarlos Del PozoIsabel ApariciMaría Sánchez-rosellóClemes Dialersubject
chemistry.chemical_classificationReaction conditionsHydrocarbons FluorinatedMolecular StructureProlineOrganic ChemistryDiastereomerBiochemistryCatalysisAmino acidStereocenterchemistryNucleophileIntramolecular forceOrganic chemistryPhysical and Theoretical ChemistryAmino AcidsSelectivityCarbaniondescription
The ability of 2-p-tolylbenzyl carbanions to behave as a source of chiral benzylic nucleophiles has been shown in its reaction with fluorinated imines. The process takes place with high levels of stereocontrol, rendering the corresponding amines as single diastereoisomers. Subsequent cross-metathesis followed by intramolecular aza-Michael reaction makes the synthesis of fluorinated homoproline derivatives bearing three stereogenic centers possible. Furthermore, the selectivity of the cyclization process can easily be tuned up in a diastereodivergent manner simply by changing the reaction conditions.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-10-21 | Organic letters |