6533b82ffe1ef96bd1294775
RESEARCH PRODUCT
Catalytic Asymmetric Formal [3+2] Cycloaddition of 2-Isocyanatomalonate Esters and Unsaturated Imines: Synthesis of Highly Substituted Chiral γ-Lactams.
Gonzalo BlayLuz CardonaM. Carmen MuñozMiguel EspinosaJosé R. Pedrosubject
Double bondLactamsStereochemistryMolecular ConformationStereoisomerismEnantioselectivityAlkenes010402 general chemistryCrystallography X-Ray01 natural sciencesCatalysisCatàlisiCoordination ComplexesAsymmetric catalysisMagnesiumPyrrolidinoneschemistry.chemical_classificationNucleophilic additionCycloaddition Reaction010405 organic chemistryNitrogen heterocyclesOrganic ChemistryEnantioselective synthesisEstersStereoisomerismGeneral ChemistryCycloadditionMalonates0104 chemical scienceschemistryFISICA APLICADAElectrophileIminesEnantiomerNucleophilic additionQuímica orgànicaIsocyanatesdescription
[EN] Unlike their isocyano and isothiocyanato analogues, isocyanato esters remain almost unexplored as formal 1,3-dipoles in asymmetric catalytic reactions. The first asymmetric formal [3+2] cycloaddition involving isocyanato esters and electrophilic alkenes is reported. Diisopropyl 2-isocyanatomalonate reacts with a,b-unsaturated N-(o-anisidyl) imines in the presence of a Mg(OTf)2¿BOX complex to give highly substituted chiral pyrrolidinones featuring a conjugate exocyclic double bond with excellent yields and enantiomeric excesses up to 99%. Several transformations of the resulting heterocycles, including the synthesis of a pyroglutamic acid derivative, have been carried out.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-01-01 | Chemistry (Weinheim an der Bergstrasse, Germany) |