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N-Heterocyclic Carbene (NHC)-Catalyzed Intermolecular Hydroacylation of Cyclopropenes

Xavier Bugaut, Fan Liu and Frank Glorius*

*Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany, Email: gloriusuni-muenster.de

X. Bugaut, F. Liu, F. Glorius, J. Am. Chem. Soc., 2011, 133, 8130-8133.

DOI: 10.1021/ja202594g (free Supporting Information)


Abstract

Treatment of aromatic aldehydes with cyclopropenes under mild NHC-catalyzed conditions affords valuable acylcyclopropanes in moderate to high yields with an excellent level of diastereocontrol. Preliminary mechanistic studies suggest that product formation occurs via a concerted syn hydroacylation pathway.


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Key Words

Cyclopropanes, Organocatalysis


ID: J48-Y2011-1530