Silicon Grignard Reagents as Nucleophiles in Transition-Metal-Catalyzed Allylic Substitution

2018/10/22 by Weichao Xue, Martin Oestreich · 2 citations
Chemistry · #Allylic rearrangement #Asymmetric Synthesis and Catalysis #Catalysis #Catalytic Cross-Coupling Reactions #Chemistry #Combinatorial chemistry #Cyclopropane Reaction Mechanisms #Electrophile #Leaving group #Medicinal chemistry #Nucleophile #Organic chemistry #Reagent #Silicon #Stereoselectivity #Substitution reaction #Transition metal

paper · pdf · doi:10.1055/s-0037-1610309

openalex publication_date 2018/10/22 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/25

Abstract

A broad range of transition-metal catalysts is shown to promote allylic substitution reactions of allylic electrophiles with silicon Grignard reagents. The procedure was further elaborated for CuI as catalyst. The regioselectively is independent of the leaving group for primary allylic precursors, favoring α over γ. The stereochemical course of this allylic transposition was probed with a cyclic system, and anti-dia­stereoselectivity was obtained.

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