One-pot synthesis of 3-functionalized (Z)-silyl enol ethers from 1-arylallylic alcohols by C,O-difunctionalization of dipotassio α,β-dianion intermediates†,10.1039/D3OB00199G

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

One-pot synthesis of 3-functionalized (Z)-silyl enol ethers from 1-arylallylic alcohols by C,O-difunctionalization of dipotassio α,β-dianion intermediates†

Rikuo Hayashi,Yutaka Narita,Masahiro Sai

Organic & Biomolecular Chemistry Pub Date : 05/02/2023 00:00:00 , DOI:10.1039/D3OB00199G

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 key to the success of this transformation. Control experiments confirmed that the dianion has higher nucleophilicity and thermal stability than related siloxyallylpotassiums.