One-Pot Synthesis of 3-Functionalized (Z)-Silyl Enol Ethers from 1-Arylallylic Alcohols by C,O-Difunctionalization of Dipotassio α,β-Dianion Intermediates

22 December 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Previously reported syntheses of 3-functionalized silyl enol ethers using allyloxysilanes are hindered by undesirable reactions owing to retro Brook rearrangements. In this study, various 3-functionalized (Z)-silyl enol ethers were synthesized from readily available 1-arylallylic alcohols using (trimethylsilyl)methylpotassium as a base. C,O-Difunctionalization of the in-situ-generated dipotassio α,β-dianion with electrophiles and silyl chlorides is the key to the success of this transformation. Control experiments confirmed that the dianion has higher nucleophilicity and thermal stability than related siloxyallylpotassiums.

Keywords

potassium
silyl enol ethers
dianions
homoenolates
enolates

Supplementary materials

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Supporting Information
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General information, experimental procedures, characterization data, and NMR spectra.
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