Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4‐Addition of Zinc‐Based Silicon Nucleophiles
Ming Cui, Martin Oestreich
Abstract
Abstract A copper‐catalyzed conjugate silylation of various cyclobutenone derivatives with Me 2 PhSiZnCl ⋅ 2LiCl or (Me 2 PhSi) 2 Zn ⋅ x LiCl ( x ≤4) to generate β‐silylated cyclobutanones is reported. Trapping the intermediate enolate with ClP(O)(OPh) 2 affords silylated enol phosphates that can be further engaged in Kumada cross‐coupling reactions to yield silylated cyclobutene derivatives.
Topics & Concepts
CyclobuteneCyclobutanoneNucleophileZincSiliconChemistryMedicinal chemistryOrganic chemistryCatalysisRing (chemistry)Synthetic Organic Chemistry MethodsOrganoboron and organosilicon chemistryAsymmetric Synthesis and Catalysis