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Synfacts 2006(7): 0690-0690  
DOI: 10.1055/s-2006-941819
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cyclic Ethers through a Catalyzed Resolution/Oxidative Cyclization

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
A. Blanc, F. D. Toste*
University of California, Berkeley, USA
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

This is a very nice follow-up paper to a previously reported kinetic resolution ofα-hydroxy esters by Toste and co-workers (J. Am. Chem. Soc. 2005, 127, 1090-1091). A variety of enantioenriched tetrahydrofurans and tetrahydropyrans can be accessed by this method. High diastereoselectivities and enantioselectivies were obtained through careful optimization of the conditions. Acetone was found to be the solvent of choice, giving the best yields of the desired products.