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

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journal contribution
posted on 26.04.2007, 00:00 authored by Xiaogen Huang, Margarita Ortiz-Marciales, Kun Huang, Viatcheslav Stepanenko, Francisco G. Merced, Angel M. Ayala, Wildeliz Correa, Melvin De Jesús
The enantioselective borane reduction of O-benzyloxime ethers to primary amines was studied under catalytic conditions using the spiroborate esters 510 derived from nonracemic 1,2-amino alcohols and ethylene glycol. Effective catalytic conditions were achieved using only 10% of catalyst 5 derived from diphenylvalinol in dioxane at 0 °C resulting in complete conversion to the corresponding primary amine in up to 99% ee.