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- W2065187006 abstract "Der lithiierte Bislactimether 2a von cyclo(-L-Val-Ala-) reagiert mit den Acrylsäureestern 7–9, die in β-Stellung eine Fluchtgruppe tragen, in einem Additions-Eliminierungs-Prozeß zu den „Michael-Addukten”︁ 10. Die asymmetrischen Induktionen sind sehr hoch (teilweise 99%). Durch Hydrolyse der Verbindungen 10 erhält man die nahezu enantiomerenreinen (R)-β,γ-Didehydro-α-methylglutaminsäure-dimethylester 13 oder die (R)-2,5-Dihydro-2-methyl-5-oxo-2-pyrrolcarbonsäure-methylester 15. – Der lithiierte Bislactimether 2b von cyclo(-L-Val-Gly) reagiert zwar mit den Acrylsäureestern 7–9 gleichartig, doch isomerisieren die Ad-dukte 11 nachträglich sehr leicht zu den Verbindungen 16, den Vorstufen für α,β-Didehydroglutaminsäure-dimethylester des Typs 17. Asymmetric Syntheses via Heterocyclic Intermediates, XXXVI. – Asymmetric Synthesis of Dimethyl (R)-4-Amino-4-methyl-2-pentenedioates (Dimethyl β,γ-Didehydro-α-methyl-D-glutamates) or Methyl (R)-2,5-Dihydro-2-methyl-5-oxo-2-pyrrolecarboxylates by the Bislactim Ether Method. – Studies on the Asymmetric Synthesis of β,γ-Didehydroglutamic Acids The lithiated bislactim ether 2a of cyclo(-L-Val-Ala-) reacts with the methyl acrylates 7–9 that carry a leaving group in β position, to give in an addition-elimination process the „Michael adducts”︁ 10. The degree of the asymmetric inductions is exceptionally high (partly 99%). On hydrolysis the compounds 10 furnish the (virtually enantiomerically pure) dimethyl (R)-β,γ-didehydro-α-methylglutamates 13 or methyl (R)-2,5-dihydro-2-methyl-5-oxo-2-pyrrole carboxylates 15. – The lithiated bislactim ether 2b of cyclo-(-L-Val-Gly-) reacts with the acrylates 7–9 analogously to give initially the „Michael adducts”︁ 11. However, these isomerize readily to yield the compounds 16, the precursors of dimethyl α,β-didehydroglutamates of type 17." @default.
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- W2065187006 date "1988-01-25" @default.
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- W2065187006 title "Asymmetrische Synthesen über heterocyclische Zwischenstufen, XXXVI. Asymmetrische Synthese von (R)-4-Amino-4-methyl-2-pentendisäuredimethylestern (β,γ-Didehydro-α-methyl-D-glutaminsäure-dimethylester) oder (R)-2,5-Dihydro-2-methyl-5-oxo-2-pyrrolcarbonsäure-methylester nach der Bislactimether-Methode. – Studien zur asymmetrischen Synthese von β,γ-Didehydroglutaminsäuren" @default.
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