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Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation

[Image: see text] A dynamic kinetic resolution of β-halo α-keto esters in an asymmetric homoenolate reaction is described. A chiral N-hetereocyclic carbene catalyzes the a(3) → d(3)-umpolung addition of α,β-enals to racemic α-keto esters, forming γ-butyrolactones with three contiguous stereocenters....

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Detalles Bibliográficos
Autores principales: Goodman, C. Guy, Walker, Morgan M., Johnson, Jeffrey S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4304455/
https://www.ncbi.nlm.nih.gov/pubmed/25533016
http://dx.doi.org/10.1021/ja511701j
Descripción
Sumario:[Image: see text] A dynamic kinetic resolution of β-halo α-keto esters in an asymmetric homoenolate reaction is described. A chiral N-hetereocyclic carbene catalyzes the a(3) → d(3)-umpolung addition of α,β-enals to racemic α-keto esters, forming γ-butyrolactones with three contiguous stereocenters. The addition occurs with high regio-, diastereo-, and enantiocontrol. This methodology constitutes an intermolecular DKR process to set three stereocenters during the key bond forming event.