A convenient synthesis of 3,4-cis-disubstituted pyrrolidin-2-ones

A convenient synthesis of 3,4-cis-disubstituted pyrrolidin-2-ones

[Display omitted] The conjugate addition of primary amines in methanol at 0°C to the difunctionalized O-methyl allyl ether, prepared from dimethyl α-(bromomethyl)fumarate, provides an adduct which cyclizes via a 5-exo-trig process to yield a new family of 3,4-cis-disubstituted pyrrolidin-2-ones in h...

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Veröffentlicht in:Tetrahedron letters 2015-01, Vol.56 (1), p.98-100
Hauptverfasser: Arfaoui, Aïcha, Saâdi, Fatma, Smida, Youssef Ben, Arfaoui, Youssef, Nefzi, Adel, Amri, Hassen
Format: Artikel
Sprache:eng
Schlagworte:
3,4-cis-Disubstituted pyrrolidin-2-ones
Adducts
Amines
Conjugates
Dimethyl
Dimethyl 3-methoxyitaconate
Dimethyl α-(bromomethyl)fumarate
Ethers
Methyl alcohol
Michael addition
Synthesis (chemistry)
Tetrahedrons
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Zusammenfassung:[Display omitted] The conjugate addition of primary amines in methanol at 0°C to the difunctionalized O-methyl allyl ether, prepared from dimethyl α-(bromomethyl)fumarate, provides an adduct which cyclizes via a 5-exo-trig process to yield a new family of 3,4-cis-disubstituted pyrrolidin-2-ones in high yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.11.023