Asymmetric Synthesis of Primary Amines via the Spiroborate-Catalyzed Borane Reduction of Oxime Ethers

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• 作者：Xiaogen Huang ; Margarita Ortiz-Marciales ; Kun Huang ; Viatcheslav Stepanenko ; Francisco G. Merced ; Angel M. Ayala ; Wildeliz Correa ; Melvin De Jesú ; s
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：April 26, 2007
• 年：2007
• 卷：9
• 期：9
• 页码：1793 - 1795
• 全文大小：68K
• 年卷期：v.9,no.9(April 26, 2007)
• ISSN：1523-7052

文摘

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The enantioselective borane reduction of O-benzyloxime ethers to primary amines was studied under catalytic conditions using the spiroborateesters 5-10 derived from nonracemic 1,2-amino alcohols and ethylene glycol. Effective catalytic conditions were achieved using only 10% ofcatalyst 5 derived from diphenylvalinol in dioxane at 0 C resulting in complete conversion to the corresponding primary amine in up to 99%ee.