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Synfacts 2007(1): 0071-0071  
DOI: 10.1055/s-2006-955736
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

2,5-Disubstituted Furans via Diastereoselective Friedel-Crafts Reaction

Contributor(s): Mark Lautens, Frédéric Ménard
P. Kwiatkowski, J. Majer, W. Chaadaj, J. Jurczak*
Polish Academy of Sciences, Warsaw and Warsaw University, Poland
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

Using phenylmenthol as a chiral auxiliary, optically active 2-furylcarbinols 3 can be prepared. The method is a mild alternative to the addition of 2-lithiated furans to carbonyls. Based on a precedent procedure (O. Achmatowicz, Jr., M. H. BurzynŽska Carbohydr. Res. 1985, 141, 67-76), SnCl4 was shown to impart excellent diastereoselectivity, but the yields were variable (41-87%). The authors found that hydrated MgBr2 showed inferior diastereoselectivities, but reliably high yields were obtained. The MgBr2-catalyzed reaction offers the advantages of being conducted at r.t., without the need to dry the solvent or work under inert atmosphere.