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Synfacts 2007(10): 1075-1075  
DOI: 10.1055/s-2007-983860
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Fluorinated Indanones via Nazarov Cyclization

Contributor(s): Mark Lautens, Frédéric Ménard
J. Nie, H.-W. Zhu, H.-F. Cui, M.-Q. Hua, J.-A. Ma*
Tianjin University and Shanghai Institute of Organic Chemistry, P. R. of China
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Publikationsdatum:
07. November 2007 (online)

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Significance

A Cu-catalyzed Nazarov cyclization was joined in a tandem reaction with a diastereoselective fluorination step. Using polarized enones as substrates in the presence of an electrophilic fluo­rine source, it is possible to obtain a range of trans-2,3-substituted indanones 2. The diastereoselectivity was reliably high, with fluorine adding on the face opposite the 3-aryl group.