Rhodium-Catalyzed Asymmetric Allenylation of Sulfonylimines and Application to the Stereospecific Allylic Allenylation

The rhodium‐catalyzed asymmetric allenylation of sulfonylimines is disclosed providing silyl homoallenylamide products in up to 99:1 er. Through subsequent activation of the C−N bond of the silyl homoallenyl sulfonamide, palladium‐catalyzed stereospecific allylic allenylation could be achieved givin...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2016-10, Vol.358 (19), p.3062-3068
Main Authors: Sieber, Joshua D., Angeles-Dunham, Veronica V., Chennamadhavuni, Divya, Fandrick, Daniel R., Haddad, Nizar, Grinberg, Nelu, Kurouski, Dimitry, Lee, Heewon, Song, Jinhua J., Yee, Nathan K., Mattson, Anita E., Senanayake, Chris H.
Format: Article
Language:English
Subjects:
Activation
allylic alkylation
asymmetric allenylation
Asymmetry
Bonding
Carbon-carbon composites
Catalysis
palladium
phosphorus ligands
Rhodium
Synthesis
Utilities
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Summary:The rhodium‐catalyzed asymmetric allenylation of sulfonylimines is disclosed providing silyl homoallenylamide products in up to 99:1 er. Through subsequent activation of the C−N bond of the silyl homoallenyl sulfonamide, palladium‐catalyzed stereospecific allylic allenylation could be achieved giving C−C bond formation with high chirality transfer. The synthetic utility of both the silyl homoallenyl sulfonamides and the silyl homoallenyl malonates as bis(nucleophiles) is demonstrated.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600686