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α‐β Unsaturated Acylsilanes as Surrogates of Acrolein for Morita–Baylis–Hillman Reactions
Author(s) -
Marri Gangababu,
Justaud Frédéric,
Das Saibal,
Grée René
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801343
Subject(s) - acrolein , adduct , chemistry , baylis–hillman reaction , acetone , addition reaction , organic chemistry , methyl vinyl ketone , catalysis
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.