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Updated: Aug 6, 2026
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Enantioselective Hydrosilylation of Diverse Allenes via Nickel Catalysis
Jin-Ping Wang1,2, Qing-Yan Wu1, Tao Liu1
1State Key Laboratory of Organometallic Chemistry and Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, People's Republic of China.
Abstract:
Enantioselective hydrosilylation of allenes remains a significant challenge with a limited scope due to the difficulties in controlling both regioselectivities and enantioselectivities, despite it representing one of the most efficient manners for the preparation of optically pure allylsilanes. Here, we report a general platform for the efficient and modular preparation of diverse allylsilanes via nickel-catalyzed hydrosilylation of various allene derivatives, including mono-substituted allenes and 1,3-disubstituted allenes. Enabled by a newly developed SPSiOL-derived diphosphinite ligand (SPSiOP), hydrosilylation of mono-substituted allenes has been realized with excellent regioselectivity and enantioselectivity. Moreover, the first kinetic resolution of racemic 1,3-disubstituted allenes has been disclosed using a commercially available chiral QuinoxP* ligand, affording a series of secondary allylsilanes with high stereo induction (S factor up to 133). The resulting enantioenriched allylsilanes are highly synthetically useful, which has been demonstrated by a variety of transformations of the silyl and alkene functional groups, culminating in efficient synthesis of silacycles and formal synthesis of several bioactive molecules.
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