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Highly Efficient Asymmetric Synthesis of Vinylic Amino Alcohols by Zn-Promoted Benzoyloxyallylation of Chiral N-tert-Butanesulfinyl Imines: Facile and Rapid Access to (−)-Cytoxazone

Authors

  • Min Liu,

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-5080-7388
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  • Xing-Wen Sun Dr.,

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-5080-7388
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  • Ming-Hua Xu Prof. Dr.,

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-5080-7388
    2. Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zuchongzhi Road, Shanghai 201203 (China)
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  • Guo-Qiang Lin Prof.

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-5080-7388
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Abstract

An efficient and convenient α-hydroxyallylation approach for the asymmetric synthesis of a variety of β-amino-α-vinyl alcohols has been successfully developed. A wide range of vinylic amino alcohol derivatives could be obtained in very good yields and with excellent diastereomeric ratios of up to 99:1 in favor of anti isomers by highly diastereoselective Zn-promoted benzoyloxyallylation of chiral N-tert-butanesulfinyl imines with 3-bromopropenyl benzoate at room temperature. In particular, excellent enantioinduction of the two new stereogenic centers was observed, with up to 98 % ee. The method provides a new route for the direct α-hydroxyallylation of imines in a highly stereoselective manner. Moreover, the synthetic value of the method has also been demonstrated by the most concise and straightforward synthesis of (−)-cytoxazone yet reported.

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