92964-64-2Relevant academic research and scientific papers
Synthesis of Morita-Baylis-Hillman-type adducts by unprecedented reaction of 1-phenyl-2-(trimethylsilyl)acetylene with aromatic aldehydes catalyzed by quaternary ammonium fluorides derived from cinchonine
Yoshizawa, Kazuhiro,Shioiri, Takayuki
, p. 7059 - 7063 (2005)
The quaternary ammonium fluoride derived from cinchonine efficiently catalyzed the reaction of 1-phenyl-2-(trimethylsilyl)acetylene with aromatic aldehydes to give the β-branched Morita-Baylis-Hillman-type adducts.
Morita-Baylis-Hillman Reaction of β,β-Disubstituted Enones: An Enantioselective Organocatalytic Approach for the Synthesis of Cyclopenta[b]annulated Arenes and Heteroarenes
Satpathi, Bishnupada,Ramasastry
supporting information, p. 1777 - 1781 (2016/02/03)
The first enantioselective organocatalytic intramolecular Morita-Baylis-Hillman (MBH) reaction of sterically highly demanding β,β-disubstituted enones is presented. The MBH reaction of β,β-disubstituted-α,β-unsaturated electron-withdrawing systems was previously considered to be unfeasible. Towards this end, designer substrates, which under simple and practical reaction conditions generate a variety of cyclopenta[b]annulated arenes and heteroarenes in excellent enantiopurities and near-quantitative yields in remarkably short reaction times, are described. The reason for the unusually facile nature of this reaction is attributed to the synergy guided and entropically favored intramolecular reaction. Further, this strategy provides easy access to a substantial number of bioactive natural products and pharmaceutically significant compounds.
