Catalytic, Asymmetric, “Interrupted” Feist−Bénary Reactions

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 enantiosele...

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Veröffentlicht in:Journal of the American Chemical Society 2005-10, Vol.127 (42), p.14566-14567
Hauptverfasser: Calter, Michael A, Phillips, Ryan M, Flaschenriem, Christine
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja055752d