Asymmetric Synthesis of Primary Amines via the Spiroborate-Catalyzed Borane Reduction of Oxime Ethers
Organic Letters2007Vol. 9(9), pp. 1793–1795
Citations Over TimeTop 10% of 2007 papers
Xiaogen Huang, Margarita Ortiz‐Marciales, Kun Huang, Viatcheslav Stepanenko, Francisco G. Merced, Angel M. Ayala, Wildeliz Correa, Melvin De Jesús
Abstract
[reaction: see text] The enantioselective borane reduction of O-benzyloxime ethers to primary amines was studied under catalytic conditions using the spiroborate esters 5-10 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 degrees C resulting in complete conversion to the corresponding primary amine in up to 99% ee.
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