Synfacts 2006(8): 0803-0803  
DOI: 10.1055/s-2006-941918
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Formation of Functionalized 2,5-Dihydrofurans

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
A. Buzas, F. Istrate, F. Gagosz*
Ecole Polytechnique, Palaiseau, France
Further Information

Publication History

Publication Date:
21 July 2006 (online)

Significance

Optically active starting materials are smoothly converted into the corresponding 2,5-dihydrofurans with high levels of chirality transfer. Primary, secondary, and tertiary alcohol groups gave high yields in all cases. For the reaction using chiral starting materials, only the primary alcohols did not show high chirality transfer. The reaction proceeds through an allenyl intermediate which is cyclized by the gold(I) catalyst to generate the product.