6533b86ffe1ef96bd12cd482
RESEARCH PRODUCT
Diastereoselective Intramolecular Additions of Allyl- and Propargylsilanes to Iminium Ions: Synthesis of Cyclic and Bicyclic Quaternary Amino Acids
Santos FusteroJose Luis AcenaAntonio Simón-fuentesNatalia Mateusubject
StereochemistryMetathesisBiochemistrychemistry.chemical_compoundheterocyclic compoundsAmino AcidsPhysical and Theoretical ChemistryPipecolic acidIonschemistry.chemical_classificationChiral auxiliaryMolecular StructureBicyclic moleculeorganic chemicalsOrganic ChemistryIminiumStereoisomerismSilanesAmino acidAllyl CompoundschemistryCyclizationAlkynesIntramolecular forceIminesHydroaminationdescription
Chiral imino lactones derived from (R)-phenylglycinol containing an allyl- or propargyltrimethylsilyl group in the side chain readily cyclized in the presence of acidic reagents to afford spirocyclic compounds with high diastereoselectivity. Removal of the chiral auxiliary produced 2-substituted 1-aminocycloalkanecarboxylic acids, whereas further cyclizations by means of metathesis or hydroamination reactions led to bicyclic derivatives of pipecolic acid and proline.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-01-01 |