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Bu4N+-Controlled Addition and Olefination with Ethyl 2-(Trimethylsilyl)acetate via Silicon Activation

Manas Das, Atul Manvar, Ian Fox, Dilwyn J. Roberts, Donal F. O'Shea*

*Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2, Ireland, Email: donalfoshearcsi.ie

M. Das, A. Manvar, I. Fox, D. J. Roberts, D. F. O'Shea, Synlett, 2017, 28, 2401-2406.

DOI: 10.1055/s-0036-1588805


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Abstract

Catalytic Bu4NOAc as silicon activator of ethyl 2-(trimethylsilyl)acetate enables the synthesis of β-hydroxy esters, whereas catalytic Bu4NOTMS provides α,β-unsaturated esters. The established reaction conditions were applicable to a diverse range of aromatic, heteroaromatic, aliphatic aldehydes and ketones.

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Key Words

tetrabutyl ammonium, acetate, trimethylsilyl oxide, silicon activation, addition, olefination, β-hydroxy esters


ID: J60-Y2017