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Asymmetric Catalytic Synthesis of Enantiopure N-Protected 1,2-Amino Alcohols

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    Asymmetric Catalytic Synthesis of Enantiopure N-Protected 1,2-Amino Alcohols
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    Department of Organic Chemistry “A. Mangini”, University of Bologna v.le Risorgimento 4, 40136 Bologna, Italy
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    Cite this: Org. Lett. 2004, 6, 22, 3973–3975
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    https://doi.org/10.1021/ol048322l
    Published October 1, 2004
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    Abstract

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    The asymmetric aminolytic kinetic resolution (AKR) of racemic terminal epoxides using carbamates as the nucleophile catalyzed by (salen)CoIII complex provides a practical and straightforward method for the synthesis of both aliphatic and aromatic N-Boc- or N-Cbz-protected 1,2-amino alcohols in almost enantiomerically pure form (ee ≥ 99%). The AKR uses an easily accessible catalyst and inexpensive starting materials, and the reactions are conveniently carried out at room temperature under an air atmosphere.

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    Cite this: Org. Lett. 2004, 6, 22, 3973–3975
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    https://doi.org/10.1021/ol048322l
    Published October 1, 2004
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