Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland–Claisen Rearrangement

[Image: see text] A dianionic Ireland–Claisen rearrangement of chiral, nonracemic α-methyl-β-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential util...

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Detalles Bibliográficos
Autores principales: Crimmins, Michael T., Knight, John D., Williams, Philip S., Zhang, Yan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4018138/
https://www.ncbi.nlm.nih.gov/pubmed/24735235
http://dx.doi.org/10.1021/ol5008422
Descripción
Sumario:[Image: see text] A dianionic Ireland–Claisen rearrangement of chiral, nonracemic α-methyl-β-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential utility of the rearrangement for complex molecule synthesis is also demonstrated.

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