6533b851fe1ef96bd12a8c6f
RESEARCH PRODUCT
ChemInform Abstract: Diastereodivergent Synthesis of Fluorinated Cyclic β3-Amino Acid Derivatives.
Clemens DialerMaría Sánchez-rosellóCarlos Del PozoSantos FusteroMarta GuerolaAntonio Simón-fuentesIsabel Aparicisubject
chemistry.chemical_classificationchemistryNucleophileIntramolecular forceSalt metathesis reactionDiastereomerGeneral MedicineSelectivityCombinatorial chemistryCarbanionAmino acidStereocenterdescription
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 |
|---|---|---|---|---|
| 2016-03-01 | ChemInform |