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Synfacts 2009(9): 0992-0992  
DOI: 10.1055/s-0029-1217624
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of α-Hydroxyallenes by SN2′ of Propargylic Dioxolanones

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
X. Tang, S. Woodward*, N. Krause
The University of Nottingham, UK and Technische Universität Dortmund, Germany
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Publication History

Publication Date:
21 August 2009 (online)

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Significance

This paper described a new catalytic method for the synthesis of α-hydroxyallenes by copper(I)-catalyzed SN2′ reaction of propargylic dioxolanones with Grignard reagents. A variety of primary and secondary α-hydroxyallenes were obtained with good to excellent yields via a highly anti-selective pathway. Moreover, this method could be applied to the synthesis of enantiomerically enriched allenes with complete chirality transfer.