Catalytic, Asymmetric, “Interrupted” Feist−Bénary Reactions
Journal of the American Chemical Society2005Vol. 127(42), pp. 14566–14567
Citations Over TimeTop 14% of 2005 papers
Abstract
Pyrimidine derivatives of the cinchona alkaloids function as excellent asymmetric catalysts for the "Interrupted" Feist-Bénary Reaction. This reaction produces highly substituted hydroxydihydrofurans from simple starting materials under mild conditions. The asymmetric reaction gives high enantioselectivities with unsubstituted bromoketones, and high enantio- and diastereoselectivities with substituted substrates. Mechanistic experiments suggest that the hydrobromide salt of the alkaloid derivative is the active catalyst for the reaction.
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