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

abstract

• 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim The rhodium-catalyzed asymmetric allenylation of sulfonylimines is disclosed providing silyl homoallenylamide products in up to 99:1 er. Through subsequent activation of the CN bond of the silyl homoallenyl sulfonamide, palladium-catalyzed stereospecific allylic allenylation could be achieved giving CC 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. (Figure presented.).

authors

• Kurouski, Dzmitry

published proceedings

• ADVANCED SYNTHESIS & CATALYSIS

author list (cited authors)

• Sieber, J. D., Angeles-Dunham, V. V., Chennamadhavuni, D., Fandrick, D. R., Haddad, N., Grinberg, N., ... Senanayake, C. H.

citation count

• 18

complete list of 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

publication date

• October 2016

publisher

• Wiley  Publisher

published in

• Advanced Synthesis and Catalysis  Journal

keywords

• Allylic Alkylation
• Asymmetric Allenylation
• Palladium
• Phosphorus Ligands
• Rhodium

Digital Object Identifier (DOI)

• 10.1002/adsc.201600686

start page

• 3062

end page

• 3068

volume

• 358

issue

• 19

URL

• http://dx.doi.org/10.1002/adsc.201600686