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Ligand-Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides
Mojtaba Hajiloo Shayegan1, Zhong-Yuan Li1, Xin Cui1
1Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA.
Abstract:
Ligand-controlled regiodivergence has been developed for catalytic semireduction of allenamides with excellent chemo- and stereocontrol. This system also provides an example of catalytic regiodivergent semireduction of allenes for the first time. The divergence of the semireduction is enabled by ligand switch with the same palladium pre-catalyst under operationally simple and mild conditions. Monodentate ligand XPhos exclusively promotes selective 1,2-semireduction to afford allylic amides, while bidentate ligand BINAP completely switched the regioselectivity to 2,3-semireduction, producing (E)-enamide derivatives.
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