Regio- and diastereoselective synthesis of unsymmetrical 1,4-diketone-derived (Z)-monosilyl enol ethers via siloxyallylpotassium intermediates

Shuto Okuda; Yutaka Narita; Rikuo Hayashi; Masahiro Sai

doi:10.1039/d2cc07097a

Regio- and diastereoselective synthesis of unsymmetrical 1,4-diketone-derived (Z)-monosilyl enol ethers via siloxyallylpotassium intermediates

Chem Commun (Camb). 2023 Mar 7;59(20):2939-2942. doi: 10.1039/d2cc07097a.

Authors

Shuto Okuda¹, Yutaka Narita¹, Rikuo Hayashi¹, Masahiro Sai¹

Affiliation

¹ Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan. msai@gifu-u.ac.jp.

PMID: 36799249
DOI: 10.1039/d2cc07097a

Abstract

This paper describes the regio- and diastereoselective synthesis of unsymmetrical 1,4-diketone-derived (Z)-monosilyl enol ethers from 1-arylallyloxysilanes and Weinreb amides using (trimethylsilyl)methylpotassium as a base. The metalation of 1-arylallyloxysilanes to generate siloxyallylpotassiums is the key step in this transformation. The products can be transformed into diverse α-monofunctionalized unsymmetrical 1,4-diketones.