Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji–Trost Cascade Cyclization

[Image: see text] A stereoselective intramolecular Tsuji–Trost cascade cyclization of (homo)allylic vicinal diacetates with a pendant β-ketoamide or related carbon nucleophile to give γ-lactam-fused vinylcyclopropanes is reported. In addition to two new rings, the products contain three new C–C ster...

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Detalles Bibliográficos
Autores principales: Braun, John, Ariëns, Maxim I., Matsuo, Bianca T., de Vries, Steven, van Wordragen, Ellen D. H., Ellenbroek, Brecht D., Vande Velde, Christophe M. L., Orru, Romano V. A., Ruijter, Eelco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6218879/
https://www.ncbi.nlm.nih.gov/pubmed/30350659
http://dx.doi.org/10.1021/acs.orglett.8b02232
Descripción
Sumario:[Image: see text] A stereoselective intramolecular Tsuji–Trost cascade cyclization of (homo)allylic vicinal diacetates with a pendant β-ketoamide or related carbon nucleophile to give γ-lactam-fused vinylcyclopropanes is reported. In addition to two new rings, the products contain three new C–C stereocenters (two of which are quaternary) with a 9:1 dr. Moreover, the reaction proceeds in >94% enantiospecificity with optically enriched starting materials, using an inexpensive carbohydrate as the source of chirality.

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