Synthesis of Silyl Dienol Ethers via Peterson Olefination of Siloxyallylpotassium Species
Year: 2025
Type: article
Abstract: We report a general method for synthesizing a diverse array of silyl dienol ethers via the Peterson olefination of aldehydes and benzophenone using 3-silyl-substituted siloxyallylpotassium species. The reaction proceeds smoothly at −78 °C and tolerates a wide range of functional groups on the aldehyde substrate (OMe, NMe 2, F, Cl, Br, CN, CO 2 t Bu, CF 3, and epoxide). Under our conditions, organolithium bases are ineffective, underscoring the critical role of potassium carbanions. The resulting silyl dienol ethers are readily converted to β,γ-unsaturated ketones. This two-step sequence thus constitutes a formal β-olefination of ketones.
Source: Organic Letters
Author: Masahiro Sai
Institution: Shimane University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Funder: Tokuyama Science Foundation
OpenAlex ID: W4416015007