Palladium-Catalyzed Preparation of Silyl Enolates from α,β-Unsaturated Ketones or Cyclopropyl Ketones with Hydrosilanes

2009/09/18 by Yuto Sumida, Hideki Yorimitsu, Koichiro Oshima · 61 citations
Chemistry · #Catalysis #Catalytic Cross-Coupling Reactions #Chemistry #Citation #Computer science #Cyclopropane Reaction Mechanisms #Library science #Organic chemistry #Organoboron and organosilicon chemistry #Silylation #Social media #World Wide Web

paper · doi:10.1021/jo901513v

published in The Journal of Organic Chemistry 74(20), 7986-7989 (American Chemical Society)

openalex publication_date 2009/09/18 · openalex created_date 2016/06/24 · openalex updated_date 2026/07/28

Abstract

Alpha,beta-unsaturated ketones and cyclopropyl ketones undergo palladium-catalyzed hydrosilylation with hydrosilanes to yield (Z)-silyl enolates.

Citations

• Hydrosilylation of enones: platinum divinyltetramethyldisiloxane complex in the preparation of triisopropylsilyl and triphenylsilyl enol ethers

Cited by

• Modular access to complex prodiginines: total synthesis of (+)-roseophilin via its 2-azafulvene prototropisomer. [europepmc]
• Stereospecific Si-C coupling and remote control of axial chirality by enantioselective palladium-catalyzed hydrosilylation of maleimides. [europepmc]
• Selective Synthesis of Z -Silyl Enol Ethers via Ni-Catalyzed Remote Functionalization of Ketones. [europepmc]
• Silyl formates as hydrosilane surrogates for the transfer hydrosilylation of ketones. [europepmc]
• C(alkyl)-C(vinyl) bond cleavage enabled by Retro-Pallada-Diels-Alder reaction. [europepmc]
• Unified Total Synthesis of the Limonoid Alkaloids: Strategies for the De Novo Synthesis of Highly Substituted Pyridine Scaffolds. [europepmc]
• A Cooperative Cobalt-Driven System for One-Carbon Extension in the Synthesis of ( Z )-Silyl Enol Ethers from Aldehydes: Unlocking Regio- and Stereoselectivity. [europepmc]
• Synthesis of Oxasilolanes by TBAT-Catalyzed Hydroxyl-Directed Hydrosilylation. [europepmc]

Related

• Ligand -controlled nickel-catalyzed C–O bond cleavage of silyl enol ether for the divergent synthesis of aryl alkenes and silicon-containing product
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