Enantioselective Aminosilylation of Alkenes by Palladium/Ming‐Phos‐Catalyzed Tandem Narasaka–Heck/Silylation Reaction
Source abstract
Abstract
Abstract A Pd‐catalyzed enantioselective aminosilylation of alkenes via tandem Aza‐Heck/silylation reaction under Pd/Sadphos catalysis is disclosed. A wide array of oxime esters and silicon reagents are tolerated, furnishing the chiral pyrrolines bearing one quaternary or two contiguous stereocenters in good yield with high enantioselectivity. Not only terminal alkenes but also tri‐substituented internal alkenes successfully participate in the reaction, delivering vicinal stereocenters in complete diastereoselectivity and high enantioselectivity. DFT study is conducted to probe the reaction pathway and the origin of the enantioselectivity, which revealed that the stereoinduction arises from the weak interaction between the aromatic ring of the substrate fragment and naphthyl group in the ligand.
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Research context
OpenAlex topics: Catalytic C–H Functionalization Methods · Organoboron and organosilicon chemistry · Synthesis and Catalytic Reactions
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Engineering Center of Catalysis and Synthesis for Chiral Molecules Department of Chemistry Fudan University Shanghai Shanghai 200433 China
School of Chemical & Environmental Science Shaanxi University of Technology Hanzhong 723001 China
Department of Chemistry Fudan University 2005 Songhu Road Shanghai 200438 China
School of Chemistry and Chemical Engineering Henan Normal University Xinxiang Henan 453007 China
Zhuhai Fudan Innovation Institute Zhuhai 519000 China
Funding
National Key Research and Development Program of China · National Natural Science Foundation of China · Science and Technology Commission of Shanghai Municipality · Shanghai Municipal Education Commission
References (100+)
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