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Synfacts 2010(5): 0565-0565  
DOI: 10.1055/s-0029-1219639
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Ruthenium-Catalyzed Oxidative Cylization of 5,6-Dihydroxy Alkenes

Contributor(s): Hisashi Yamamoto, Jiajing Tan
H. Cheng, C. B. W. Stark*
Freie Universität Berlin and Universität Leipzig, Germany
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

Previously, the authors reported a ruthenium tetraoxide catalyzed oxidative cyclization reaction of 1,5-dienes (Eur. J. Org. Chem. 2005, 4109) which can be utilized to synthesize diastereochemically pure THF diols efficiently. As an extension of the previous report, this work presented a pathway to synthesize enantiomerically pure THF diols. The target THF diols were obtained in moderate yield as well as high diastereoselectivities and enantioselectivities.