Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters

A Ni(ClO(4))(2)-catalyzed enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines was developed, which regioselectively occurred at the proximal C[double bond, length as m-dash]C bonds of the N-allenamides. Broad substrate scope of N-allenamides and cyclic N-sulfonylk...

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Detalles Bibliográficos
Autores principales: Liu, Ren-Rong, Hu, Jiang-Ping, Hong, Jian-Jun, Lu, Chuan-Jun, Gao, Jian-Rong, Jia, Yi-Xia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5427681/
https://www.ncbi.nlm.nih.gov/pubmed/28553518
http://dx.doi.org/10.1039/c6sc05450a
Descripción
Sumario:A Ni(ClO(4))(2)-catalyzed enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines was developed, which regioselectively occurred at the proximal C[double bond, length as m-dash]C bonds of the N-allenamides. Broad substrate scope of N-allenamides and cyclic N-sulfonylketimines was observed. A range of fused polysubstituted azetidines bearing quaternary stereocenters were afforded in good yields and with excellent enantioselectivities (up to 99%).

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