Abstract
The Morita-Baylis-Hillman (MBH) reaction of aryl vinyl ketones has been achieved for the first time through cooperative catalysis of proline and brucine N-oxide. A unique mode of activation of the aldehydes through proline iminium intermediates has been identified as a key reaction parameter for the successful MBH reaction of aryl vinyl ketones. The reaction pathways leading to 1:2 MBH products under typical nucleophilic catalysis conditions were investigated. A systematic study revealed two different reaction pathways leading to 1:2 MBH products: (1) the second reaction of normal MBH products with aryl vinyl ketones as a dominating reaction pathway at the initial stage of the reaction, and (2) the aldol reaction pathway of Rauhut-Currier products with aldehydes (auto-catalysis by alcohol products) as a major reaction pathway during the later stage of reaction.
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