Ring‐Opening Regio‐, Diastereo‐, and Enantioselective 1,3‐Chlorochalcogenation of Cyclopropyl Carbaldehydes

meso‐Cyclopropyl carbaldehydes are treated in the presence of an organocatalyst with sulfenyl and selenyl chlorides to afford 1,3‐chlorochalcogenated products. The transformation is achieved by a merged iminium–enamine activation. The enantioselective desymmetrization reaction, leading to three adja...

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Detalles Bibliográficos
Autores principales: Wallbaum, Jan, Garve, Lennart K. B., Jones, Peter G., Werz, Daniel B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6680189/
https://www.ncbi.nlm.nih.gov/pubmed/27868248
http://dx.doi.org/10.1002/chem.201605265
Descripción
Sumario:meso‐Cyclopropyl carbaldehydes are treated in the presence of an organocatalyst with sulfenyl and selenyl chlorides to afford 1,3‐chlorochalcogenated products. The transformation is achieved by a merged iminium–enamine activation. The enantioselective desymmetrization reaction, leading to three adjacent stereocenters, furnished the target products in complete regioselectivity and moderate to high diastereo‐ and enantioselectivities (d.r. up to 15:1 and e.r. up to 93:7).

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