Dynamic resolution of α-halo chiral esters for the synthesis of 3-substituted piperazin-2-ones

Dynamic resolution of α-halo chiral esters for the synthesis of 3-substituted piperazin-2-ones

Dynamic resolution of α-halo esters derived from five chiral alcohols has been investigated in nucleophilic substitution with ethylenediamine nucleophiles. Stereoselective substitution of α-halo esters and following spontaneous cyclization provide a practical protocol for asymmetric syntheses of 3-s...

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Veröffentlicht in:Tetrahedron 2011-08, Vol.67 (34), p.6221-6226
Hauptverfasser: Jang, Jung In, Kang, Seock Yong, Kang, Kyoung Hee, Park, Yong Sun
Format: Artikel
Sprache:eng
Schlagworte:
Asymmetric synthesis
Asymmetry
Chemistry
Chiral auxiliary
Dynamic resolution
Dynamic tests
Dynamics
Esters
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Nucleophiles
Nucleophilic substitution
Organic chemistry
Piperazinone
Preparations and properties
Spontaneous
Synthesis (chemistry)
Tetrahedrons
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Zusammenfassung:Dynamic resolution of α-halo esters derived from five chiral alcohols has been investigated in nucleophilic substitution with ethylenediamine nucleophiles. Stereoselective substitution of α-halo esters and following spontaneous cyclization provide a practical protocol for asymmetric syntheses of 3-substituted piperazin-2-ones up to 94:6 er. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.06.055