α-β Unsaturated Acylsilanes as Surrogates of Acrolein for Morita-Baylis-Hillman Reactions

Gangababu Marri; Frédéric Justaud; Saibal Das; René Grée

doi:10.1002/ejoc.201801343

Journal articles

α-β Unsaturated Acylsilanes as Surrogates of Acrolein for Morita-Baylis-Hillman Reactions

Gangababu Marri ¹ Frédéric Justaud ² Saibal Das ^{1, *} René Grée ^{2, *}

* Corresponding author

1 Division of Natural Products Chemistry

2 ISCR - Institut des Sciences Chimiques de Rennes

Abstract : α‐β‐unsaturated acylsilanes are excellent substrates for Morita–Baylis–Hillman (MBH) reactions, affording the expected adducts in good to excellent yields. In these derivatives, as well as the corresponding acetates, the acylsilanes can be smoothly transformed into aldehydes by irradiation at 365 nm in acetone or THF/water mixtures. Therefore α‐β unsaturated acylsilanes are very useful surrogates for acrolein in MBH reactions, allowing easy preparation of simple and highly functionalized new building blocks for synthetic applications.

Keywords : Morita–Baylis–Hillman Enals Acylsilanes Rauhut‐Currier Photolysis

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Journal articles

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Chemical Sciences / Organic chemistry

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α-β Unsaturated Acylsilanes as Surrogates of Acrolein for Morita-Baylis-Hillman Reactions

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α-β Unsaturated Acylsilanes as Surrogates of Acrolein for Morita-Baylis-Hillman Reactions

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