Nickel-catalyzed switchable 1,3-dienylation and enantioselective allenylation of phosphine oxides

Jiayin Zhang, Xihao Chang, Xianghong Xu, Hongyi Wang, Lingzi Peng and Chang Guo ()
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Jiayin Zhang: University of Science and Technology of China
Xihao Chang: University of Science and Technology of China
Xianghong Xu: University of Science and Technology of China
Hongyi Wang: University of Science and Technology of China
Lingzi Peng: University of Science and Technology of China
Chang Guo: University of Science and Technology of China

Nature Communications, 2022, vol. 13, issue 1, 1-11

Abstract: Abstract The development of general catalytic methods for the regio- and stereoselective construction of phosphoryl derivatives from identical substrates remains a formidable challenge in organic synthesis. Enabled by the newly developed BDPP-type ligands, we disclosed a nickel-catalyzed allenylation of phosphine oxides rationally and predictably, allowing the construction of versatile chiral allenylphosphoryl derivatives with high enantiopurity (up to 94% e.e.). Alternatively, using an achiral phosphine ligand dcypbz under acidic conditions, we achieved a regiochemical switch of the 1,3-dienylation to afford functionalized phosphinoyl 1,3-butadienes (up to 93% yield). The salient features of this method include switchable reactivity, broad substrate scope, readily available feedstock, single-step preparation, and high asymmetric induction.

Date: 2022
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DOI: 10.1038/s41467-022-34764-x

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