10.1021/ja055752d.s001
Michael A. Calter
Michael A.
Calter
Ryan M. Phillips
Ryan M.
Phillips
Christine Flaschenriem
Christine
Flaschenriem
Catalytic, Asymmetric, “Interrupted” Feist−Bénary Reactions
American Chemical Society
2005
Feist
cinchona alkaloids function
hydrobromide salt
unsubstituted bromoketones
Interrupted
catalyst
Mechanistic experiments
2005-10-26 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Catalytic_Asymmetric_Interrupted_Feist_B_nary_Reactions/3261373
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.