Organic Letters 2007-04-26

Asymmetric synthesis of primary amines via the spiroborate-catalyzed borane reduction of oxime ethers.

Xiaogen Huang, Margarita Ortiz-Marciales, Kun Huang, Viatcheslav Stepanenko, Francisco G Merced, Angel M Ayala, Wildeliz Correa, Melvin De Jesús

Index: Org. Lett. 9(9) , 1793-5, (2007)

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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.