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Synfacts 2008(5): 0501-0501  
DOI: 10.1055/s-2008-1072661
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Zinc-Catalyzed Asymmetric Friedel-Crafts Alkylation of Pyrroles

Contributor(s): Mark Lautens, Praew Thansandote
B. M. Trost*, C. Müller
Stanford University, USA
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Publikationsdatum:
23. April 2008 (online)

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Significance

A dinuclear zinc catalyst has been used for the asymmetric Friedel-Crafts alkylation of pyrroles with nitroalkenes. The reaction is regio­selective for the 2-position of the pyrrole and a domino reaction is used to form 2,5-disubstituted pyrroles. Good enantioselectivities and yields are seen for a variety of nitroalkenes, including those with aryl, heteroaryl, and alkyl substituents.