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)

1 Division of Natural Products Chemistry
2 ISCR - Institut des Sciences Chimiques de Rennes

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; Acylsilanes; Rauhut‐Currier; Photolysis; Enals

Domains: Chemical Sciences; Organic chemistry

Gangababu Marri, Frédéric Justaud, Saibal Das, René Grée. α-β Unsaturated Acylsilanes as Surrogates of Acrolein for Morita-Baylis-Hillman Reactions. European Journal of Organic Chemistry, 2019, 2019 (1), pp.56-65. ⟨10.1002/ejoc.201801343⟩. ⟨hal-01944076⟩